Studies on Chrysanthemic Acid Part XVII. Stereospecific Synthesis of Optically Pure (+)-trans-Chrysanthemic Acid from (+)Δ3-Carene

Masanao MATSUI; Hirosuke YOSHIOKA; Hideo SAKAMOTO; Yasuhiro YAMADA; Takeshi KITAHARA

doi:10.1271/bbb1961.31.33

Studies on Chrysanthemic Acid

Part XVII. Stereospecific Synthesis of Optically Pure (+)-trans-Chrysanthemic Acid from (+)Δ³-Carene

Masanao MATSUI, Hirosuke YOSHIOKA, Hideo SAKAMOTO, Yasuhiro YAMADA, Takeshi KITAHARA

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ジャーナルフリー

1967 年 31 巻 1 号 p. 33-39

DOI https://doi.org/10.1271/bbb1961.31.33

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抄録

Pure (+)-trans-chrysanthemic acid was synthesized from (+)-Δ³-carene.
Ozonolysis of (+)-Δ³-carene affords 2, 2-dimethyl-3-(2-oxo-propyl)-cyclopropyl-acetalde-hyde which was cyclized to (-1-)-2-acetyl-6, 6-dimethyl-bicyclo-[3, 1, 0]-2-hexene. The bicyclo compound was transformed into (+)-cis-homocaronic acid by ozonolysis followed by oxid-ation. Diester or anhydride of the acid and methyl magnesium iodide gave (-)-dihydro-chrysanthemolactone which afforded finally (+)-trans-chrysanthemic acid via ethyl (-)-cis-chrysanthemate.

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