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Paper | Regular issue | Vol 32, No. 5, 1991, pp.879-888
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5361
Asymmetric Synthesis XXV. Diastereoselective Synthesis of Indolizidinediol Alkaloid Analogs

Virginie Ratovelomanana, Laurent Vidal, Jacques Royer, and Henri-Philippe Husson*

*Institut de Chimie des Substances Naturelles, C.N.R.S., 1 avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France

Abstract

The asymmetric synthesis of 3-methylindolizidine-1,2-diol, analog of indolizidine-1,2-diol alkaloids, has been achieved from the chiral 2-cyano-6-oxazolopiperidine synthon (1). The synthesis commenced with 1,2 addition of the anion of 1 on crotonaldehyde leading to 8 with enantioselective formation of the firtst hydroxyl group. Epoxidation of the double bond followed by hydrogenolysis of the benzyl appendage led to the amino epoxides (13). Finally the five membered ring construction was accomplished by employing cyclization of 13.