pentalenolactone E

Base Information

• Chemical Name: pentalenolactone E
• CAS No.: 89163-60-0
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.306
• Mol file: 89163-60-0.mol

Synonyms:

Chemical Property of pentalenolactone E

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pentalenolactone E

There total 15 articles about pentalenolactone E which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-pentalenen-6-ol (89111-51-3) → pentalenolactone E (72715-03-8,89163-60-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 71 percent / hydroboration-oxidation

2: 87 percent / 15 h / 85 °C

3: 86 percent / SeO₂ / ethanol / 24 h / Heating

4: NaCN/MnO₂/AcOH / room temp., 18 h

5: 78 percent / 0 °C / Jones oxidation

6: 1.) TMSOTf, Et₃N; 2.) NBS / 1.) benzene, room temp., 10 min; 2.) THF, 5 min

7: 30 percent / Et₃N, NaHCO₃ / benzene / 24 h / Ambient temperature

8: 80 percent / (TMS)2NH / benzene / 2 h / Ambient temperature

9: 1.) mCPBA; 2.) NaIO₄ / 1.) hexane, - 15 deg C, 30 min; room temp., 2h; 2.) H₂O-t-BuOH, room temp., 4h

10: 1.) NaBH₄; 2.) 2N HCl / 1.) EtOH, 0 degC, 10 min; 2.) pH 2, room temp., 2 h

11: 1.) LiOH; 2.) 1N HCl / 1.) H₂O-THF, room temp.; 2.) pH 2, room temp., 2 h

With hydrogenchloride; manganese(IV) oxide; lithium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; selenium(IV) oxide; trimethylsilyl trifluoromethanesulfonate; sodium cyanide; sodium hydrogencarbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol; benzene;

DOI:10.1016/S0040-4039(00)94293-X

Reference yield:

(1R,2R,3aR,4S,5aR,8aS)-1,4,7,7-Tetramethyl-octahydro-cyclopenta[c]pentalene-2,3a-diol (89111-52-4,89163-66-6) → pentalenolactone E (72715-03-8,89163-60-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 87 percent / 15 h / 85 °C

2: 86 percent / SeO₂ / ethanol / 24 h / Heating

3: NaCN/MnO₂/AcOH / room temp., 18 h

4: 78 percent / 0 °C / Jones oxidation

5: 1.) TMSOTf, Et₃N; 2.) NBS / 1.) benzene, room temp., 10 min; 2.) THF, 5 min

6: 30 percent / Et₃N, NaHCO₃ / benzene / 24 h / Ambient temperature

7: 80 percent / (TMS)2NH / benzene / 2 h / Ambient temperature

8: 1.) mCPBA; 2.) NaIO₄ / 1.) hexane, - 15 deg C, 30 min; room temp., 2h; 2.) H₂O-t-BuOH, room temp., 4h

9: 1.) NaBH₄; 2.) 2N HCl / 1.) EtOH, 0 degC, 10 min; 2.) pH 2, room temp., 2 h

10: 1.) LiOH; 2.) 1N HCl / 1.) H₂O-THF, room temp.; 2.) pH 2, room temp., 2 h

With hydrogenchloride; manganese(IV) oxide; lithium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; selenium(IV) oxide; trimethylsilyl trifluoromethanesulfonate; sodium cyanide; sodium hydrogencarbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol; benzene;

DOI:10.1016/S0040-4039(00)94293-X

Reference yield:

(Z)-(3aR,4R,9aR)-4-Methoxy-2,2,4,8-tetramethyl-2,3,3a,4,5,6,9,9a-octahydro-1H-cyclopentacyclooctene (80786-92-1,89163-64-4) → pentalenolactone E (72715-03-8,89163-60-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) hydroboration-oxidation; 2.) Jones oxidation

2: 1.) formic acid; 2.) sodium carbonate / 1.) 45 grad C, 2h: 2.) methanol-water, room temp., 6h

3: 71 percent / hydroboration-oxidation

4: 87 percent / 15 h / 85 °C

5: 86 percent / SeO₂ / ethanol / 24 h / Heating

6: NaCN/MnO₂/AcOH / room temp., 18 h

7: 78 percent / 0 °C / Jones oxidation

8: 1.) TMSOTf, Et₃N; 2.) NBS / 1.) benzene, room temp., 10 min; 2.) THF, 5 min

9: 30 percent / Et₃N, NaHCO₃ / benzene / 24 h / Ambient temperature

10: 80 percent / (TMS)2NH / benzene / 2 h / Ambient temperature

11: 1.) mCPBA; 2.) NaIO₄ / 1.) hexane, - 15 deg C, 30 min; room temp., 2h; 2.) H₂O-t-BuOH, room temp., 4h

12: 1.) NaBH₄; 2.) 2N HCl / 1.) EtOH, 0 degC, 10 min; 2.) pH 2, room temp., 2 h

13: 1.) LiOH; 2.) 1N HCl / 1.) H₂O-THF, room temp.; 2.) pH 2, room temp., 2 h

With hydrogenchloride; manganese(IV) oxide; lithium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; formic acid; selenium(IV) oxide; trimethylsilyl trifluoromethanesulfonate; sodium cyanide; sodium hydrogencarbonate; sodium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol; benzene;

DOI:10.1016/S0040-4039(00)94293-X

upstream raw materials:

(+/-)-pentalenolactone E Methyl Ester

3-pentalenen-6-ol

(3aR,5aS,8aR)-7,7-Dimethyl-1-methylene-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester

(1R,3aR,5aR,8aS)-1-Bromo-1,7,7-trimethyl-2-oxo-1,2,3,3a,5a,6,7,8-octahydro-cyclopenta[c]pentalene-4-carboxylic acid methyl ester