Journal of the American Chemical Society

[3+ 2] Annulation of Allylic Silanes in Acyclic Stereocontrol: Total Synthesis of (9 S)-Dihydroerythronolide A

ZH Peng, KA Woerpel

Index: Peng, Zhi-Hui; Woerpel Journal of the American Chemical Society, 2003 , vol. 125, # 20 p. 6018 - 6019

Full Text: HTML

Citation Number: 57

Abstract

The [3+ 2] annulation reactions of allylic silanes can be utilized to achieve acyclic stereocontrol. This method was employed as a key step in an enantioselective total synthesis of (9 S)-dihydroerythronolide A. The key annulation reaction served to establish most of the stereochemistry of the target, including the two tetrasubstituted carbon stereocenters. The symmetry of the target molecule allowed it to be disconnected into two ...