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Yoshito Kishi (1937-2023)
Yoshito Kishi (1937-2023)
Professor. Yoshito Kishi,
a member of the Honorary Editorial Associates of HETEROCYCLES,
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Kunio Ogasawara
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January 13, 2023
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Paper | Regular issue | Vol 43, No. 9, 1996, pp.1981-1989
Published online, 1st January, 1970■ Claisen Orthoester Rearrangement in the Direct Preparation of Deplancheine Derivatives Possessing a Malonyl Group at C-15
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
Abstract
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.
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