Structural revision of terpenoids with a (3Z)-2-methyl-3-penten-2-ol moiety by the synthesis of (23E)- and (23Z)-cycloart-23-ene-3beta,25-diols

Shunya Takahashi; Hiroko Satoh; Yayoi Hongo; Hiroyuki Koshino

doi:10.1021/jo070478m

Structural revision of terpenoids with a (3Z)-2-methyl-3-penten-2-ol moiety by the synthesis of (23E)- and (23Z)-cycloart-23-ene-3beta,25-diols

J Org Chem. 2007 Jun 8;72(12):4578-81. doi: 10.1021/jo070478m. Epub 2007 May 17.

Authors

Shunya Takahashi¹, Hiroko Satoh, Yayoi Hongo, Hiroyuki Koshino

Affiliation

¹ RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan. shunyat@riken.jp

PMID: 17506582
DOI: 10.1021/jo070478m

Abstract

Synthesis of (23E)-cycloart-23-ene-3beta,25-diol (1) and its 23Z-isomer 2 was achieved by using cycloartenol as a starting material, thus revising the proposed structure of natural 2 to 1 unequivocally. These synthetic studies revealed that the structural revision (Z-form --> E-form) should also be applied to terpenoids such as (23Z)-3beta-acetoxyeupha-7,23-diene-25-ol, (23Z)-tirucalla-7,23-diene-3beta,25-diol, quadrangularol A, quadrangularic acid K, and daurichromene C.

Publication types

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

MeSH terms

Nuclear Magnetic Resonance, Biomolecular / methods
Stereoisomerism
Terpenes / chemical synthesis
Terpenes / chemistry*
Triterpenes / chemical synthesis
Triterpenes / chemistry*

Substances

9,19-cycloart-23-ene-3,25-diol
Terpenes
Triterpenes