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Communication | Special issue | Vol 37, No. 2, 1994, pp.679-681
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S65
■ Total Synthesis of (±)-cis-, trans-Cembranolides (±)-Sarcophytonin B from Geranylgeraniol

Kiyoshi Nishitani, Toshihiko Konomi, Kiyonobu Okada, and Koji Yamakawa*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 12, Ichigaya Funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan

Abstract

(±)-cis-Cembranolide (I) was synthesized via Cr(II) mediated intramolecular macrocyclization of ω-formyl-β-methoxycarbonylallyl halides (6a and b), which were prepared starting from geranylgeraniol. The stereoselective synthesis of (±)-trans-cembranolide (II) was achieved by lactonization of 14-membered cis-intermediate (7) with inversion of the stereochemistry at C-2. (±)-Sarcophytonin B (III) was also synthesized from (±)-cis-cembranolide (I) via isomerization of the exo-cyclic double bond.