Stereospecific synthesis of 2, 3, 6-trisubstituted piperidines: an efficient total synthesis of (.+-.)-pumiliotoxin C

NA LeBel, N Balasubramanian

Index: LeBel, Norman A.; Balasubramanian, N. Journal of the American Chemical Society, 1989 , vol. 111, # 9 p. 3363 - 3368

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Citation Number: 58

Abstract

Abstract: The intramolecular cycloaddition of N-(1-alkyl-4-pentenyl) nitrones provides a highly regio-and stereoselective route to all-cis-2, 6-disubstituted-3-(hydroxymethyl) piperidines 3 by way of the bicyclic isoxazolidines 2. In demonstration studies, the 2.6- dimethyl analogue was transformed into 2r, 3~, 6~-trimethyIpiperidine(9) and into N-tert- butoxy-2~, 6c-dimethyI-piperidine-3r-carboxaldehyde (10). Facile and complete ...