Synthesis of ceramide analogues having the C (4)-C (5) bond of the long-chain base as part of an aromatic or heteroaromatic system

J Chun, L He, HS Byun, R Bittman

Index: Chun, Jiong; He, Linli; Byun, Hoe-Sup; Bittman, Robert Journal of Organic Chemistry, 2000 , vol. 65, # 22 p. 7634 - 7640

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Citation Number: 52

Abstract

Two efficient and stereoselective methods are described for the preparation of aryl and heteroaryl ceramide analogues 2 and 3. The first route involves the addition of an aryllithium or a heteroaryllithium reagent (7a or 25a, respectively) to the l-serine-derived aldehyde 4, followed by hydrolysis of the oxazolidine, liberation of the amino group, and N-acylation. The second route, which was used to prepare arylceramide analogue 2 in eight steps and 28 ...