Ormosia alkaloids. VII. Total synthesis of ormosanine, piptanthine, 18-epiormosanine, and d,l-panamine
- 1 January 1976
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 54 (1) , 97-109
- https://doi.org/10.1139/v76-017
Abstract
A stereoselective synthesis of ormosanine (1), identical in all respects with the naturally occurring racemic alkaloid of O. jamaicensis, has been accomplished. Subsequent transformation of synthetic ormosanine into racemic piptanthine (2) and into d,l-panamine (3) is described. 18-Epiormosanine (22) has also been prepared by total synthesis. Some unusual stereochemical effects allowing the control of configuration at C6, C11, and C18 are discussed.This publication has 4 references indexed in Scilit:
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- The identity of piptamine and ormosanine, and the structures of ormojanine, ormosinine and panamineTetrahedron, 1965
- A Simple Modification of the Wolff-Kishner ReductionJournal of the American Chemical Society, 1946