73466-12-3

Usage

Uses

Used in Pharmaceutical Industry:
(-)-Leukotriene A4 Methyl Ester is used as a key intermediate compound for the synthesis of other biologically active leukotrienes, such as LTB4 and LTC4. These leukotrienes are involved in various physiological processes, including inflammation, immune response, and blood clotting. The study and development of LTA4 and its derivatives can lead to the creation of new therapeutic agents for treating conditions related to these processes.
Used in Research and Development:
In the field of biomedical research, (-)-Leukotriene A4 Methyl Ester serves as an important tool for understanding the role of leukotrienes in cellular signaling and their involvement in various diseases. Researchers can use LTA4 as a stable source to study the enzymatic reactions and pathways involved in leukotriene biosynthesis, as well as to investigate the potential therapeutic applications of leukotrienes and their analogs.
Used in Drug Delivery Systems:
Similar to gallotannin, (-)-Leukotriene A4 Methyl Ester can be incorporated into novel drug delivery systems to enhance its bioavailability and therapeutic outcomes. By employing various organic and metallic nanoparticles as carriers, the delivery, efficacy, and targeting of LTA4 to specific cells or tissues can be improved, potentially leading to more effective treatments for conditions related to leukotriene dysregulation.

Synthetic route

<(Z)-3-nonenyl>triphenyl phosphonium tosylate (82393-41-7) + (5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester (73958-00-6) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;	90%

(5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester (73958-00-6) + Phosphorane of (Z)-3-nonen-1-yl-triphenylphosponium bromide (73958-09-5) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃;	88%

<(3Z)-nonen-1-yl>triphenylphosphonium iodide (72297-07-5) + (5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester (73958-00-6) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Wittig reaction;	63%
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide
With n-butyllithium 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min; Yield given. Multistep reaction;

(S)-5-hydroperoxy-6-trans,8,11,14-cis-eicosatetraenoic acid methyl ester (75331-81-6) → Leukotriene A4 methyl ester (73466-12-3) + methyl (6E,8Z,11Z,14Z)-5-oxo-6,8,11,14-eicosatetraenoate (74785-00-5)

Conditions	Yield
With 1,2,2,6,6-pentamethylpiperidine; trifluoromethanesulfonic acid anhydride In diethyl ether; dichloromethane at -110℃; for 0.666667h;	A 25% B n/a

diazomethane (186581-53-3, 908094-01-9) + 6-epi-Leukotriene A4 (71548-17-9, 72059-45-1, 74497-09-9, 76375-76-3, 77341-35-6, 114129-55-4, 114129-56-5, 114129-57-6) → Leukotriene A4 methyl ester (73466-12-3) + 5S,6R-6-epi-Leukotriene A4 methyl ester (76738-49-3) + 5R,6S-6-epi-Leukotriene A4 methyl ester (79356-68-6) + 5-epi-6-epi-leukotriene A4 methyl ester (79356-65-3)

Conditions	Yield
In diethyl ether at 0℃; for 0.166667h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

methyl 5(S),6(S)-oxido-11-oxo-7-cis-9-trans-undecadienoate (82442-92-0) + Phosphorane of (Z)-3-nonen-1-yl-triphenylphosponium bromide (73958-09-5) → Leukotriene A4 methyl ester (73466-12-3) + 7-cis-leukotriene A4 methyl ester (82467-14-9)

Conditions	Yield
In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; for 0.333333h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester (73958-00-6) + triphenyl <(Z)-non-3-en-1-yl>phosphonium chloride (75415-25-7) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Yield given;

(5S,6S)-epoxy-11,14-eicosadiyne-7E,9E-dienoate (118333-88-3) → Leukotriene A4 methyl ester (73466-12-3) + 13,14-dehydro-leukotriene A4 methyl ester (82850-12-2) + 4-[(2S,3S)-((1E,3E,8Z)-3-Tetradeca-1,3,8-trien-5-ynyl)-oxiranyl]-butyric acid methyl ester (118333-83-8)

Conditions	Yield
With pyridine; hydrogen; Lindlar's catalyst In hexane at 20℃; under 750.06 Torr; Yields of byproduct given;	A 5.5 mg B n/a C n/a
With pyridine; hydrogen; Lindlar's catalyst In hexane at 20℃; under 750.06 Torr; Yield given;	A 5.5 mg B n/a C n/a

(-)-(S,S-trans)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester (73957-99-0) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 68 percent / Py2*CrO3; 4 Angstroem molecular sieves / CH2Cl2 2: CH2Cl2 / 15 h 3: I2 / CH2Cl2 / 1 h 4: 63 percent / nBuLi; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C View Scheme
Multi-step reaction with 3 steps 1: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 2: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 3: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 3 steps 1: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 2: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 3: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 3 steps 1: 63 percent / CrO3/Py / CH2Cl2 2: 70 percent 3: 90 percent / n-BuLi / tetrahydrofuran / -78 °C View Scheme
Multi-step reaction with 3 steps 1: 50 percent / Collins oxidation View Scheme

(+)-(S,R-trans)-3-formyloxiranebutanoic acid methyl ester (73427-12-0) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: CH2Cl2 / 15 h 2: I2 / CH2Cl2 / 1 h 3: 63 percent / nBuLi; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 2: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 2 steps 1: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 2: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

7-acetoxy-(5S,6S)-epoxyheptanoic acid methyl ester (76871-82-4) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 69 percent / K2CO3; Na2SO4 / methanol / 0.17 h / 20 °C 2: 68 percent / Py2*CrO3; 4 Angstroem molecular sieves / CH2Cl2 3: CH2Cl2 / 15 h 4: I2 / CH2Cl2 / 1 h 5: 63 percent / nBuLi; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C View Scheme

(5S,6S)-epoxy-10-formyl-(9E)-decadienoic acid methyl ester (73958-00-6, 76738-48-2, 77341-38-9, 79356-64-2, 79356-67-5, 82442-92-0, 92009-26-2) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: I2 / CH2Cl2 / 1 h 2: 63 percent / nBuLi; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1: iodine 2: BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide View Scheme

7-acetoxy-(5S,6S)-epoxyheptanoic acid → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: diethyl ether / 0.08 h / 0 °C 2: 69 percent / K2CO3; Na2SO4 / methanol / 0.17 h / 20 °C 3: 68 percent / Py2*CrO3; 4 Angstroem molecular sieves / CH2Cl2 4: CH2Cl2 / 15 h 5: I2 / CH2Cl2 / 1 h 6: 63 percent / nBuLi; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C View Scheme

3-nonyn-1-ol (31333-13-8) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 96.4 percent / hydrogen, quinoline / Lindlar catalyst / hexane / 1.25 h 2: 97.1 percent / pyridine / 1.5 h / 0 - 5 °C 3: 95 percent / sodium iodide / acetone / 67 h / Ambient temperature 4: 11.2 g / benzene / 43 h / 80 °C 5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(Z)-non-3-en-1-ol (10340-23-5) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 97.1 percent / pyridine / 1.5 h / 0 - 5 °C 2: 95 percent / sodium iodide / acetone / 67 h / Ambient temperature 3: 11.2 g / benzene / 43 h / 80 °C 4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

[(4R,5S)-5-((Z)-3-[1,3]Dioxan-2-yl-propenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol (85612-85-7) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 9 steps 1: 40.8 g / pyridine / 3 h / 5 °C 2: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 3: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 4: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 5: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 6: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 8: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 9: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 9 steps 1: 40.8 g / pyridine / 3 h / 5 °C 2: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 3: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 4: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 5: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 6: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 8: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 9: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

3-cis-nonene-1-yl-p-toluenesulfonate (72297-08-6) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / sodium iodide / acetone / 67 h / Ambient temperature 2: 11.2 g / benzene / 43 h / 80 °C 3: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(1’R)-(-)-4,6-O-ethylidene-D-glucose (13224-97-0, 13224-98-1, 13224-99-2, 13225-00-8, 13225-01-9, 13225-02-0, 18465-50-4, 87068-63-1) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 10 steps 1: NaIO4, aq. sodium hydroxide / H2O / 0.25 h / 5 - 10 °C / pH 4 2: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C 3: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 4: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 5: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 6: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 7: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 8: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 9: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 10: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 10 steps 1: NaIO4, aq. sodium hydroxide / H2O / 0.25 h / 5 - 10 °C / pH 4 2: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C 3: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 4: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 5: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 6: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 7: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 8: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 9: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 10: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(+)--6-<2-<(benzoyloxy)-1-hydroxy>ethyl>tetrahydro-2H-pyran-2-one (77332-97-9) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 2: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 4: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 5 steps 1: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 2: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 4: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Benzoic acid (R)-2-methanesulfonyloxy-2-((S)-6-oxo-tetrahydro-pyran-2-yl)-ethyl ester (77332-98-0) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 3: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 4 steps 1: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 3: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(+)-(4S-cis)-2,2-dimethyl-5-<(benzoyloxy)methyl>-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester (77333-01-8) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 2: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 3: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 5: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 6: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 6 steps 1: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 2: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 3: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 5: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 6: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(+)-(4R-cis)-2,2-dimethyl-5-<3-(1,3-dioxan-2-yl)-1-propyl>-1,3-dioxolane-4-methanol benzoate (77333-00-7, 85648-04-0) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 7 steps 1: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 2: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 3: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 4: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 6: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 7: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 7 steps 1: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 2: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 3: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 4: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 6: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 7: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(+)-(4R-cis)(Z)-2,2-dimethyl-5-<3-(1,3-dioxan-2-yl)-1-propenyl>-1,3-dioxolane-4-methanol benzoate (77332-94-6, 77398-80-2) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 2: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 3: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 4: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 5: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 7: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 8: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 8 steps 1: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 2: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 3: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 4: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 5: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 7: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 8: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(3Z)-3-nonenyliodide (72297-09-7) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 11.2 g / benzene / 43 h / 80 °C 2: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(2R,4S,5R)-4-((E)-3-[1,3]Dioxan-2-yl-propenyl)-2-methyl-[1,3]dioxan-5-ol (85612-90-4) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 8 steps 1: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 2: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 3: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 4: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 5: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 7: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 8: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 8 steps 1: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 2: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 3: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 4: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 5: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 7: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 8: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Methanesulfonic acid (R)-2-hydroxy-1-((S)-6-oxo-tetrahydro-pyran-2-yl)-ethyl ester (85612-93-7) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 3: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 4 steps 1: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 3: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(-)-(2R,4S,5R)-4-<3-(1,3-dioxan-2-yl)propyl>-2-methyl-1,3-dioxan-5-ol methanesulfonate (85612-91-5) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 2: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 3: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 5: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 6: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 6 steps 1: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 2: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 3: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 5: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 6: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(2R,4S,5R)(E)-4-<3-(1,3-dioxan-2-yl)-1-propenyl>-2-methyl-1,3-dioxan-5-ol methanesulfonate (85612-89-1) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 7 steps 1: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 2: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 3: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 4: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 6: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 7: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 7 steps 1: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 2: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 3: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 4: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 6: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 7: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(-)-(2R,4S,5R)-2-methyl-5-<(methylsulfonyl)oxy>-1,3-dioxane-4-butanoic acid 3-hydroxypropyl ester (85612-92-6) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 2: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 4: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 5 steps 1: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 2: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 4: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

(1'R)-(-)-2,4-O-ethylidene-D-erythrose (70377-89-8) → Leukotriene A4 methyl ester (73466-12-3)

Conditions	Yield
Multi-step reaction with 9 steps 1: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C 2: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 3: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 4: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 5: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 6: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 8: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 9: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme
Multi-step reaction with 9 steps 1: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C 2: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 3: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 4: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 5: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 6: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 8: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 9: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

L-cysteine methyl ester hydrochloride (18598-63-5) + Leukotriene A4 methyl ester (73466-12-3) → leukotriene E4 dimethyl ester (74448-22-9)

Conditions	Yield
With triethylamine In methanol; water for 1h; Ambient temperature; pH 9;	94%
With triethylamine In methanol for 5h; Ring cleavage; Condensation;	75%

Leukotriene A4 methyl ester (73466-12-3) + N-(trifluoroacetyl)-L-cysteinylglycine methyl ester (75290-62-9) → N-trifluoroacetyl-leukotriene D4 dimethyl ester (76322-44-6)

Conditions	Yield
With triethylamine In methanol for 4h; Ring cleavage; Condensation;	77%

Leukotriene A4 methyl ester (73466-12-3) + methyl 6-mercapto-3(E)-hexenoate (135388-27-1) → (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-((E)-5-methoxycarbonyl-pent-3-enylsulfanyl)-icosa-7,9,11,14-tetraenoic acid methyl ester (140215-33-4)

Conditions	Yield
With sodium methylate In methanol for 3h; Ambient temperature;	71%

Oxidized glutathione (27025-41-8) + Leukotriene A4 methyl ester (73466-12-3) → Leukotriene C4 methyl ester (73958-10-8)

Conditions	Yield
With triethylamine In methanol for 12h; Condensation; Ring cleavage;	55%

GLUTATHIONE (70-18-8) + Leukotriene A4 methyl ester (73466-12-3) → (7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions	Yield
With triethylamine for 2h; Ambient temperature;

3-Dimethylaminopropanethiol (42302-17-0) + Leukotriene A4 methyl ester (73466-12-3) → (7E,9E,11Z,14Z)-(5S,6R)-6-(3-Dimethylamino-propylsulfanyl)-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (83851-65-4)

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;

1-mercapto-5-carbomethoxy-pentane (20756-86-9) + Leukotriene A4 methyl ester (73466-12-3) → (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-(5-methoxycarbonyl-pentylsulfanyl)-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions	Yield
With sodium methylate In methanol

N-Trifluoroacetylglutathione dimethyl ester (75290-61-8) + Leukotriene A4 methyl ester (73466-12-3) → (6E,8E,10E,14Z)-(S)-5-Hydroxy-12-{(R)-2-(methoxycarbonylmethyl-carbamoyl)-2-[(R)-4-methoxycarbonyl-4-(2,2,2-trifluoro-acetylamino)-butyrylamino]-ethylsulfanyl}-icosa-6,8,10,14-tetraenoic acid methyl ester (76695-80-2, 76740-25-5)

Conditions	Yield
With lithium perchlorate In tetrahydrofuran; diethyl ether at 23℃; for 12h; Yield given;

Leukotriene A4 methyl ester (73466-12-3) + methyl 6-mercapto-3(Z)-hexenoate (140215-41-4) → (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-((Z)-5-methoxycarbonyl-pent-3-enylsulfanyl)-icosa-7,9,11,14-tetraenoic acid methyl ester (140215-33-4)

Conditions	Yield
With sodium methylate In methanol Ambient temperature;

Leukotriene A4 methyl ester (73466-12-3) + (S)-4-((R)-2-Mercapto-1-methoxycarbonyl-ethylcarbamoyl)-2-(2,2,2-trifluoro-acetylamino)-butyric acid methyl ester (83851-50-7) → (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-{(R)-2-methoxycarbonyl-2-[(S)-4-methoxycarbonyl-4-(2,2,2-trifluoro-acetylamino)-butyrylamino]-ethylsulfanyl}-icosa-7,9,11,14-tetraenoic acid methyl ester (83851-62-1, 84414-54-0)

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;

Leukotriene A4 methyl ester (73466-12-3) + methyl 3-mercaptopropionylglycinate (80115-99-7) → deamino LTD4 dimethyl ester (80116-00-3)

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;	4.2 mg

Leukotriene A4 methyl ester (73466-12-3) + 3-mercaptopropionylglycinedimethylamide (83851-49-4) → (7E,9E,11Z,14Z)-(5S,6R)-6-[2-(Dimethylcarbamoylmethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;	2.3 mg

Leukotriene A4 methyl ester (73466-12-3) + [(3-Mercapto-propyl)-(2,2,2-trifluoro-acetyl)-amino]-acetic acid methyl ester (83851-52-9) → (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-{3-[methoxycarbonylmethyl-(2,2,2-trifluoro-acetyl)-amino]-propylsulfanyl}-icosa-7,9,11,14-tetraenoic acid methyl ester (83851-64-3)

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;

Leukotriene A4 methyl ester (73466-12-3) + 4-[(R)-2-Mercapto-1-(methoxycarbonylmethyl-carbamoyl)-ethylcarbamoyl]-butyric acid methyl ester (83851-48-3) → (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-[(R)-2-(4-methoxycarbonyl-butyrylamino)-2-(methoxycarbonylmethyl-carbamoyl)-ethylsulfanyl]-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;

Leukotriene A4 methyl ester (73466-12-3) + (S)-2-[(R)-3-Mercapto-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-pentanedioic acid dimethyl ester (83851-51-8) → (S)-2-[(R)-3-[(2E,4E,6Z,9Z)-(R)-1-((S)-1-Hydroxy-4-methoxycarbonyl-butyl)-pentadeca-2,4,6,9-tetraenylsulfanyl]-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-pentanedioic acid dimethyl ester (83851-63-2)

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;

Leukotriene A4 methyl ester (73466-12-3) + L-cysteinylglycine → (7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions	Yield
With triethylamine In methanol; water for 18h; Ambient temperature;

Leukotriene A4 methyl ester (73466-12-3) + glutathione → (7E,9E,11Z,14Z)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (73958-10-8, 74841-70-6, 84823-29-0, 84823-30-3, 89461-60-9, 89461-61-0, 89461-62-1, 89461-63-2, 92009-28-4, 113830-70-9, 113830-71-0, 113830-72-1)

Conditions	Yield
With triethylamine In methanol at 23℃; for 5h;

Leukotriene A4 methyl ester (73466-12-3) → leukotriene E4 (75715-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Et3N / methanol / 5 h 2: 82 percent / K2CO3 / methanol; H2O / 3.5 h / 0 °C View Scheme

Leukotriene A4 methyl ester (73466-12-3) → leukotriene D4 (73836-78-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / Et3N / methanol / 4 h 2: 82 percent / K2CO3 / methanol; H2O / 3.5 h / 0 °C View Scheme

Leukotriene A4 methyl ester (73466-12-3) → (7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid (73466-14-5, 74841-69-3, 76738-45-9, 79026-71-4, 79026-72-5, 80629-45-4, 82468-64-2, 84823-19-8, 84823-20-1, 87391-79-5, 92009-30-8, 92418-31-0, 92418-46-7, 72025-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 55 percent / Et3N / methanol / 12 h 2: 84 percent / K2CO3 / methanol; H2O / 3.5 h / 20 °C View Scheme

Upstream product

• 116237-17-3 4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester 
• 116237-18-4 4-((2R,4S,5R)-5-Methanesulfonyloxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester 
• 76745-18-1 (+)-(S,R)-δ-hydroxyoxiranepentanoic acid methyl ester 
• 79308-40-0 ethyl 2,3,4-trideoxy-D-ribo-hept-2-enoate 
• 73958-00-6 methyl 10-formyl-5,6E-epoxy-7E,9E-decadienoate 
• 73958-09-5 Phosphorane of (Z)-3-nonen-1-yl-triphenylphosponium bromide 
• 73957-99-0 (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 71774-08-8 5(S)-HPETE 
• 70377-89-8 (1'R)-(-)-2,4-O-ethylidene-D-erythrose 
• 31333-13-8 3-nonyn-1-ol 
• 73427-12-0 (+)-(S,R-trans)-3-formyloxiranebutanoic acid methyl ester 
• 73957-99-0 (-)-(S,S-trans)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester 
• 75331-81-6 (S)-5-hydroperoxy-6-trans,8,11,14-cis-eicosatetraenoic acid methyl ester 

Downstream Products

• 72059-45-1 leukotriene A4 
• 72025-60-6 (7E,9Z,11Z,14Z)-(5S,6R)-6-[(S)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 72025-60-6 (7E,9Z,11Z,14Z)-(5R,6S)-6-[(S)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 73466-14-5 (7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 79026-72-5 (5R,6S)-LTC₄ 
• 72025-60-6 5(S)-hydroxy-6(R)-glutathionyl-7,9-E-11,14-Z-eicosatetraenoic acid 
• 72025-60-6 leukotriene C4 
• 73958-10-8 (7E,9E,11Z,14Z)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester 
• 89461-64-3 7Z,9E,11E,14Z-LTE₄ methyl ester 
• 91944-21-7 7Z,9E,11E,14Z-LTD₄ methyl ester 
• 75443-89-9 7Z,9E,11E,14Z-LTE₄ 
• 73836-78-9 7Z,9E,11E,14Z-LTD₄ 
• 72025-60-6 (7E,9E,11Z,14Z)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 72025-60-6 leukotriene C1 

Relevant academic research and scientific papers

Total synthesis of leukotrienes from butadiene

The total synthesis of leukotrienes has been achieved starting from butadiene by a palladium-catalyzed telomerization at room temperature. A Sharpless catalytic asymmetric epoxidation generated the asymmetric centers with >94% ee. Simple transformations of the key intermediate 15 produced the leukotrienes LTA4 methyl ester (4), LTC4 (1), LTD4 (2) and LTE4 (3), as well as (14S, 15S)-LTA4 methyl ester (24) and the novel [2H2]-LTA4 methyl ester (28). The use of the opposite chiral director in the Sharpless catalytic asymmetric epoxidation gave the key intermediate 15a that has been used in the synthesis of the double epimers of the leukotrienes as well as LTB4.

Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediate

The pathway of biosynthesis of leukotriene A4 (LTA4, 2) from 5(S)-hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic acid (5-S-HPETE, 1) has been explored by the comparative study of (S)- and (R)-lipoxygenase (LO) enzymes as catalysts.The purified LO from potato, an S-lipoxygenase, converts (anaerobically) 1 to 2 (determined as the characteristic hydrolysis mixture of two epimeric 5,6-diols and two epimeric 5,12-diols), as previously reported by Samuelsson et al.However, the 8-R-LO from the coral Plexaura homomalla transforms 1 (anaerobically) into 6-epi-LTA4 (6).Theobserved divergence of stereopathways agrees with predictions based on the intermediacy of organoiron intermediates in enzymic lipoxygenation (Scheme I) and detailed in Schemes II and III.Further evidence for the intervention of such intermediates has been obtained by trapping experiments under pure O2 at pressures of 1-60 atm.Under O2 pressure 1 is converted by the potato LO to a new product, the bis(hydroperoxide) 7, whereas the coral LO converts 1 to the diastereomeric bis(hydroperoxide) 9.

SYNTHESIS OF TETRADEUTERATED LTA4 METHYL ESTER

Progress in GC/MS coupling in the field of lipids prompted us to prepare deuterated leukotrienes as stable standard compounds.Thus, chiral -tetradeuterated LTA4 methyl ester 4b was synthesized by reduction of the appropriate diyne precursor and will lead to the corresponding tetradeuterated peptidoleukotrienes.

A FACILE STEREOSELECTIVE SYNTHESIS OF LEUKOTRIENE A4(LTA4) METHYL ESTER

A facile synthesis of LTA4 1 methyl ester was achieved according to Scheme 1, in which the key intermediate 6 and 7 were prepared with the new procedures conveniently, stereoselectively and in good yields.

AN EFFICIENT AND SIMPLE METHOD THE CONVERSION OF 15-HPETE TO 14,15-EPETE (LIPOTRIENE A) AND 5-HPETE TO LEUKOTRIENE A AS THE METHYL ESTERS

Simple new methodology is described for the synthesis from arachidonic acid of the important eicosanoids lipotriene A methyl ester (5) and leukotriene A methyl ester (10), a key feature being the use of a novel chemical method for effecting the allylic hydroperoxide oxiranyl carbinol rearrangement.

Enantiospecific syntheses of leukotrienes C4, D4 and E4 and [14,15-3H2]leukotriene E4 dimethyl ester

A 'chiral-pool' approach was employed to synthesize various leukotrienes (slow-reacting substance of anaphylaxis, SRS-A) enantiospecifically. The pivotal (S,S)-trans-epoxy alcohol 9 was prepared by efficient and facile routes starting from erythorbic acid (D-araboascorbic acid, 13). This epoxide could also be produced starting from D-glucose. The epimeric (S,R)-cis-epoxide 38 was obtained utilizing L-tartaric acid as the chiral starting material. Elaboration of 9 into leukotriene A4 methyl ester (5) and the potassium salts of leukotrienes C4 (4a), D4 (4b), and E4 (4c) was accomplished by standard methods. These salts exhibited potent contractile activities in the in vitro guinea pig ileum assay. Reduction of 14,15-dehydroleukotriene A4 methyl ester (44) with tritium gas gave [14,15-3H2]-5 and subsequently the dimethyl ester of [14,15-3H2]leukotriene E4 having a high specific activity of 40 Ci/mmol.

CHEMICAL CONVERSION OF ARACHIDONIC ACID TO SLOW REACTING SUBSTANCES

The synthesis of slow reacting substances, leukotrienes C, D, and E, can be accomplished conveniently by a stereoselective biomimetic route.Details are provided for the conversion of 5-HPETE methyl ester 4 to leukotriene methyl ester (2) and thence to leukotrienes C and D.