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.
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.
Takahashi
Shunya
S
RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan. shunyat@riken.jp
Satoh
Hiroko
H
Hongo
Yayoi
Y
Koshino
Hiroyuki
H
D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry*; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry*
C102764:9,19-cycloart-23-ene-3,25-diol; D013729:Terpenes; D014315:Triterpenes