Abstract
Base-catalyzed reaction of the neo-clerodane diterpenoid eriocephalin ( 1) gave the derivatives 3 and 4. The formation of these compounds implies an elimination of the C-19 carbon atom of 1 as formaldehyde by a reaction and, in the case of 4, subsequent reaction of this formaldehyde with the 18-alkoxide intermediate followed by an intramolecular and stereoselective 1,4-addition of the resulting C-18-oxa-methylene alkoxide. Treatment of the derivative of eriocephalin 9 with base yielded transacetylation and hydrolysis products ( 10–14), with inversion of the configuration at the C-20 asymmetric centre. Mechanistic aspects of these transformations and the results achieved in the biological assay as insect antifeedants of these neo-clerodane derivatives are also reported.
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