(4aS,10aS)-2,3,4,4a,10,10a-Hexahydro-5,8-dihydroxy-6-methoxy-1,1,4a-trimethyl-7-isopropylphenanthren-9(1H)-one

Base Information

• Chemical Name: (4aS,10aS)-2,3,4,4a,10,10a-Hexahydro-5,8-dihydroxy-6-methoxy-1,1,4a-trimethyl-7-isopropylphenanthren-9(1H)-one
• CAS No.: 57685-31-1
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.467
• Mol file: 57685-31-1.mol

Synonyms:(4aS,10aS)-5,8-Dihydroxy-7-isopropyl-6-methoxy-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one;Inuroyleanol;

Chemical Property of (4aS,10aS)-2,3,4,4a,10,10a-Hexahydro-5,8-dihydroxy-6-methoxy-1,1,4a-trimethyl-7-isopropylphenanthren-9(1H)-one

Chemical Property:

• PSA: 66.76000
• LogP: 4.90020

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4aS,10aS)-2,3,4,4a,10,10a-Hexahydro-5,8-dihydroxy-6-methoxy-1,1,4a-trimethyl-7-isopropylphenanthren-9(1H)-one

There total 3 articles about (4aS,10aS)-2,3,4,4a,10,10a-Hexahydro-5,8-dihydroxy-6-methoxy-1,1,4a-trimethyl-7-isopropylphenanthren-9(1H)-one 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:

12-Methoxyabieta-8,12-dien-7,11,14-trion (57685-35-5) → inuroyleanol (57685-31-1)

Guidance literature:

With sodium dithionite; In acetic acid;

DOI:10.1246/bcsj.52.1459

Reference yield:

Taxochinon (21764-41-0) → inuroyleanol (57685-31-1)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) Et₂O, (ii) CrO₃, Py

2: aq. Na₂S₂O₄ / acetic acid

With sodium dithionite; In acetic acid;

DOI:10.1246/bcsj.52.1459

Reference yield:

7β-Acetoxy-12-benzoyloxyabieta-8,12-dien-11,14-dion (70905-79-2) → inuroyleanol (57685-31-1)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) aq. NaOH, MeOH, (ii) aq. HCl

2: (i) Et₂O, (ii) CrO₃, Py

3: aq. Na₂S₂O₄ / acetic acid

With sodium dithionite; In acetic acid;

DOI:10.1246/bcsj.52.1459

upstream raw materials:

12-Methoxyabieta-8,12-dien-7,11,14-trion

Taxochinon

7β-Acetoxy-12-benzoyloxyabieta-8,12-dien-11,14-dion

Refernces

10.1246/bcsj.52.1459

Takashi Matsumoto and Shogo Harada details the total synthesis of several naturally occurring tricyclic diterpenes with an abietane skeleton. The authors describe the synthesis of (+)-taxoquinone, (-)-7a-acetoxyroyleanone, (-)-dehydroroyleanone, (-)-horminone, (-)-7-oxoroyleanone, and (+)-inuroyleanol, all starting from (+)-ferruginol. The synthesis involves various chemical transformations, including methylation, oxidation with chromium trioxide, reduction with sodium borohydride, acetylation, and other reactions. The structures of the synthesized compounds were confirmed through NMR spectroscopy and other analytical methods. The study represents a significant advancement in the field of natural product synthesis, providing detailed procedures and characterizations for these complex diterpenes.

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