Total Synthesis of (−)??Salinosporamide A

Y Kaiya, J Hasegawa, T Momose…

Index: Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka Chemistry - An Asian Journal, 2011 ,  vol. 6,  # 1  p. 209 - 219

Full Text: HTML

Citation Number: 14

Abstract

Abstract A detailed description of our second-generation total synthesis of salinosporamide A is presented. Three contiguous stereocenters in the γ-lactam structure seen in the natural product were established by stereoselective functionalization of a D-arabinose scaffold, including an Overman rearrangement to generate a highly congested tetrasubstituted carbon center. One of the definitive reactions in the synthesis was a Lewis acid mediated ...