Organic Letters 2005-04-14

Synthesis of a novel ceramide analogue via Tebbe methylenation and evaluation of its antiproliferative activity.

Xuequan Lu, Gilbert Arthur, Robert Bittman

Index: Org. Lett. 7 , 1645, (2005)

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Abstract

[reaction: see text] A new analogue of (2S,3R)-ceramide (2) with a methylene group at C4 has been synthesized from d-tartaric acid (3) by using Tebbe methylenation as the key step. Compound 2 exhibited markedly higher antiproliferative activity on mouse embryonic fibroblast (MEF) cells than natural (2S,3R,4E)-ceramide (1).