(+/-)-alliacol A

Base Information

Chemical Name:(+/-)-alliacol A
CAS No.:122743-30-0
Molecular Formula:C₁₅H₂₀O₄
Molecular Weight:264.321
Hs Code.:

Synonyms:

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Chemical Property of (+/-)-alliacol A

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-alliacol A

There total 37 articles about (+/-)-alliacol A 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: 88.0%

: 79232-31-8,122743-34-4,122743-35-5
(+/-)-12-noralliacolide

: 79232-29-4,122743-30-0,122743-37-7
(+/-)-alliacol A

Guidance literature:: With 2,2,6,6-tetramethylpiperidinyl-lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; 1.) -20 to 0 deg C, 1.5 h, 2.) -20 deg C to r.t., 12 h;
DOI:10.1021/jo00120a027

Reference yield: 45.0%

: 33797-51-2
eschenmoser's salt

: 79232-31-8,122743-34-4,122743-35-5
(+/-)-12-noralliacolide

: 79232-29-4,122743-30-0,122743-37-7
(+/-)-alliacol A

Guidance literature:: With 2,2,6,6-tetramethylpiperidinyl-lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -20 - 25 ℃; for 12h;
DOI:10.1016/S0040-4039(00)82176-0

Reference yield:

: 930-30-3
cyclopent-2-enone

: 79232-29-4,122743-30-0,122743-37-7
(+/-)-alliacol A

Guidance literature:: Multi-step reaction with 22 steps

1: 77 percent / n-BuLi / 1.) THF, hexane, 20 deg C, 1 h; HMPA, -78 deg C, 30 min, 2.) -78 deg C, 24 h; 0 deg C, 1 h

2: 94 percent / 10percent HCl / tetrahydrofuran / 4 h / Heating

3: 1.) CuI / 1.) ether, THF, 0 deg C, 45 min, 2.) 0 deg C, 3 h

4: 96 percent / LDA / 1.) THF, cyclohexane, -78 deg C, 2 h; -20 deg C, 18 h, 2.) HMPA, -78 deg C, 30 min; -78 deg C, 4 h

5: 99 percent / L-Selectride / tetrahydrofuran / 3 h

6: 1.) trimethyloxonium tetrafluoroborate, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, r.t., 1.2 h, 2.) 20 min

7: 96 percent / 70percent HClO₄ / benzene; CCl₄ / 1.) 0 deg C, 15 min, 2.) 30 min

8: 85percent m-CPBA, NaHCO₃ / CH₂Cl₂ / 3 h / 0 °C

9: aq. KOH / CH₂Cl₂; methanol / 1 h / Ambient temperature

10: 96 percent / p-TsOH*H₂O / benzene / 1.5 h / Heating

11: aq. K₂CO₃ / methanol / 48 h / Ambient temperature

12: 95 percent / LDA / 1.) THF, cyclohexane, -78 deg C to r.t., 3 h, 2.) HMPA, -78 deg C, 1 h

13: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -55 deg C, 30 min, 2.) -55 deg C, 1 h; -55 to 0 deg C, 1 h

14: 98 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 0 °C

15: 48 percent / DIBAL-H / toluene; hexane / 1.5 h / -78 °C

16: LiAlH₄ / diethyl ether / 3.5 h / Ambient temperature

17: 98 percent / pyridine, DMAP / CH₂Cl₂ / 0.5 h

18: 88 percent / aq. KOH, BHT / tetrahydrofuran / 0.25 h / 0 °C

19: 89 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / 1.) -78 deg C, 2 h, 2.) r.t., 42 h

20: 98 percent / 80percent m-CPBA, Na₂CO₃ / CH₂Cl₂ / 2 h

21: 98 percent / aq. NaIO₄, aq. Na₂CO₃, aq. RuCl₃ / CCl₄; acetonitrile / 96 h / Ambient temperature

22: 88 percent / LiTMP / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1.) -20 to 0 deg C, 1.5 h, 2.) -20 deg C to r.t., 12 h

With pyridine; hydrogenchloride; dmap; ruthenium trichloride; potassium hydroxide; sodium periodate; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; 2,2,6,6-tetramethylpiperidinyl-lithium; sodium methylate; trimethoxonium tetrafluoroborate; L-Selectride; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; cyclohexane; toluene; acetonitrile; benzene;
DOI:10.1021/jo00120a027