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Paper | Regular issue | Vol 43, No. 9, 1996, pp.1981-1989
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7538
Claisen Orthoester Rearrangement in the Direct Preparation of Deplancheine Derivatives Possessing a Malonyl Group at C-15

Mauri Lounasmaa* and Pirjo Hanhinen

*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, P.O. Box 6100, FIN-02150 HUT Espoo, Finland


The Claisen orthoester rearrangement utilizing allylic alcohols (1) and (2), and triethyl ortho-2-ethoxycarbonylacetate (= ethyl triethyl orthomalonate) (4) leads directly to deplancheine derivatives (12-14) possessing a malonyl group at C-15. Compounds (12-14) represent the prototype of highly desired intermesiates for the preparation of Corynanthé alkaloids and similar compounds.