(-)-Compressanolide

Base Information

• Chemical Name: (-)-Compressanolide
• CAS No.: 68421-48-7
• Molecular Formula: C15H22O3
• Molecular Weight: 250.338
• Mol file: 68421-48-7.mol

Synonyms:(3S,3aS,6aR,9R,9aS,9bS)-9-Hydroxy-3,9-dimethyl-6-methylene-decahydro-azuleno[4,5-b]furan-2-one;(-)-compressanolide;compressanolide;(-)-4α-hydroxy-1,5,7αH,6,11βH-guai-10(14)-en-6,12-olide;

Chemical Property of (-)-Compressanolide

Chemical Property:

• PSA: 46.53000
• LogP: 2.29130

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-Compressanolide

There total 2 articles about (-)-Compressanolide 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:

gallicin (69075-77-0) + methanesulfonyl chloride (124-63-0) → isocostus lactone (38236-17-8) + 4α-hydroxy-1α,5α,6β,7α,11α-H-guaian-10(15)-en-6,12-olide mesylate (76627-94-6) + 4α-hydroxy-1α,5α,6β,7α,11α-H-guaian-10(15)-en-6,12-olide (68421-48-7) + 4β-hydroxy-1α,5α,6β,7α,11α-H-guaian-10(15)-en-6,12-olide (76820-57-0)

Guidance literature:

In pyridine; at 0 ℃; for 24h;

DOI:10.1016/0040-4020(80)80216-X

Reference yield:

isocostus lactone (38236-17-8) → 4α-hydroxy-1α,5α,6β,7α,11α-H-guaian-10(15)-en-6,12-olide (68421-48-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 60 percent / m-CPBA / CHCl₃ / 5 h / -10 °C

2.1: NaBH₄ / dimethylformamide / 2 h / 20 °C

2.2: 92 percent / AcOH; Ti(i-PrO₄) / dimethylformamide / 23 h / 20 °C

3.1: 65 percent / W-2 Raney Ni / ethanol / 0.5 h / 20 °C

With sodium tetrahydroborate; W-2 Raney Ni; 3-chloro-benzenecarboperoxoic acid; In ethanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/np020109f

Reference yield: 48.5%

4α-hydroxy-1α,5α,6β,7α,11α-H-guaian-10(15)-en-6,12-olide (68421-48-7) → isocostus lactone (38236-17-8)

Guidance literature:

With thionyl chloride; In pyridine; at 0 ℃; for 0.25h;

DOI:10.1016/0040-4020(80)80216-X

upstream raw materials:

gallicin

methanesulfonyl chloride

isocostus lactone

Downstream raw materials:

isocostus lactone

Toluene-4-sulfonic acid (3S,3aS,6R,6aS,9R,9aS,9bS)-9-hydroxy-3,9-dimethyl-2-oxo-dodecahydro-azuleno[4,5-b]furan-6-yl ester

Refernces

• 1、 Gonzalez, Antonio G.,Galindo, Antonio,Mansilla, Horacio. "Biomimetic cyclization of gallicin to form guaianolides1 1 Part 43 in the series Chemistry of the Composites. For Part 42, see: A.G. Gonzalez, A. Galindo, H. Mansilla and A. Alemany, Tetrahedron Letters 376". . p. 2015 - 2017. Retrieved 2007/10/02.