Organic & biomolecular chemistry

A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs

Y Cai, CC Ling, DR Bundle

Index: Cai, Ye; Ling, Chang-Chun; Bundle, David R. Organic and Biomolecular Chemistry, 2006 , vol. 4, # 6 p. 1140 - 1146

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Citation Number: 42

Abstract

Sphingosine, sphinganines and phytosphingosines and their analogs were synthesized by an aldol condensation between an iminoglycinate bearing a (+)-(1R, 2R, 5R)-2-hydroxy-3- pinanone group as chiral auxiliary and an appropriate aldehyde. All condensations proceeded with excellent enantioselectivity to generate the (2S, 3R)-D-erythro structures in good yields.

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