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Paper | Regular issue | Vol 43, No. 3, 1996, pp.611-617
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7335
Some Base-catalyzed Reactions of NOR-Clerodane Derivatives and Their Antifeedant Activity

Chen Huan-Ming, Min Zhi-Da,* Munekazu Iinuma, and Toshiyuki Tanaka

*Department of Pharmacognosy, Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu 502, Japan


By base-catalyzed reaction of a nor-clerodane diterpene, teucvidin (1), several cis- (5, 6) and trans-clerodane derivatives (3, 7, 8) were obtained. Their structures including stereochemistry were established by spectroscopic means and X-ray analysis of 5, and by correlation to the known products. The formation of these compounds implied that a different kind of basic reagents had influence on the stereochemistry of reactive products. Among the compounds obtained, 7 showed the most potent antifeedant activity to larvae of Leucania separata.