Asymmetric synthesis of methyl (-)-13-oxo-15,16-dinorlabda-8(17),11E-dien-19-oate, methyl ester of a potent suppressor toward carcinogenic promotor

Takahiro Katoh; Shinsuke Mizumoto; Masato Fudesaka; Tetsuya Kajimoto; Manabu Node

doi:10.1248/cpb.54.1333

Asymmetric synthesis of methyl (-)-13-oxo-15,16-dinorlabda-8(17),11E-dien-19-oate, methyl ester of a potent suppressor toward carcinogenic promotor

Chem Pharm Bull (Tokyo). 2006 Sep;54(9):1333-7. doi: 10.1248/cpb.54.1333.

Authors

Takahiro Katoh¹, Shinsuke Mizumoto, Masato Fudesaka, Tetsuya Kajimoto, Manabu Node

Affiliation

¹ Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University, Misasagi, Kyoto 607-8412, Japan.

PMID: 16946548
DOI: 10.1248/cpb.54.1333

Abstract

Asymmetric synthesis of methyl ester (4) of (-)-13-oxo-15,16-dinorlabda-8(17),11E-dien-19-oic acid (1), which exhibited the most potent activity for the prevention of incipient carcinogenesis among the isolated diterpenes from Thuja standishii and its related plants, was achieved by using methyl (-)-1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylate (5) as a strating material, which was easily prepared on gram scale by baker's yeast-catalyzed asymmetric reduction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemical synthesis*
Alkenes / chemistry
Alkenes / pharmacology*
Anticarcinogenic Agents / chemical synthesis*
Anticarcinogenic Agents / chemistry
Anticarcinogenic Agents / pharmacology*
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Diterpenes / isolation & purification
Diterpenes / pharmacology*
Molecular Conformation
Promoter Regions, Genetic / drug effects*
Stereoisomerism
Structure-Activity Relationship
Thuja / chemistry

Substances

1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylate
Alkenes
Anticarcinogenic Agents
Diterpenes
methyl-13-oxo-15,16-dinorlabda-8(17),11E-dien-19-oate