Synthetic Studies on Spirovetivane Phytoalexins. III. : A Total Synthesis of (±)-Lubiminol

Chuzo IWATA; Yoshiji TAKEMOTO; Hitoshi KUBOTA; Minoru YAMADA; Shuji UCHIDA; Tetsuaki TANAKA; Takeshi IMANISHI

doi:10.1248/cpb.37.866

Chuzo IWATA, Yoshiji TAKEMOTO, Hitoshi KUBOTA, Minoru YAMADA, Shuji UCHIDA, Tetsuaki TANAKA, Takeshi IMANISHI

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Keywords: spirovetivane sesquiterpene, phytoalexin, lubiminol, total synthesis, S_N2 reaction, sodio diethyl malonate, bis(ethoxycarbonyl)methyl group, allylic alcohol, hydride reduction, isopropenyl group

JOURNAL FREE ACCESS

1989 Volume 37 Issue 4 Pages 866-869

DOI https://doi.org/10.1248/cpb.37.866

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Abstract

A total synthesis of (±)-lubiminol (2) from the allylic alcohol (3) was achieved through the introduction of a bis(ethoxycarbonyl)methyl group with inversion at C₂ followed by hydrogenation of the C₆-C₇ double bond and transformation of the bis(ethoxycarbonyl)methyl group into isopropenyl. On the other hand, the alcohol (1) was an inefficient starting material for the synthesis.

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