Organic letters

Stereochemistry of sagittamide A: prediction and confirmation

H Seike, I Ghosh, Y Kishi

Index: Seike, Hirofumi; Ghosh, Indranath; Kishi, Yoshito Organic Letters, 2006 , vol. 8, # 17 p. 3865 - 3868

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Citation Number: 28

Abstract

The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the 3 JH, H profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed 1H NMR analysis of the two remote diastereomers, followed by doping ...