Tetrahedron letters

Determination of the relative and absolute stereochemistry of sphingofungins A, B, C, and D

…, C Dufresne, FE Wincott, RT Mosley, KE Wilson

Index: VanMiddlesworth, Frank; Dufresne, Claude; Wincott, Francine E.; Mosley, Ralph T.; Wilson, Kenneth E. Tetrahedron Letters, 1992 , vol. 33, # 3 p. 297 - 300

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Citation Number: 47

Abstract

Abstract The relative and absolute stereochemistry of positions 2, 3, 4, and 5 of the recently isolated sphingofungins has been determined as 2S, 3R, 4R, 5S by spectral analysis of the rigid bicyclic derivative 5, and enzymatic hydrolysis of 4 using a 2S specific acylase. These configurational assignments were confirmed by degradation and conversion of sphingofungin B to peracetyl deoxynojirimycin 6.