First synthesis of polyoxin M

Y Shiro, K Kato, M Fujii, Y Ida, H Akita

Index: Shiro, Yuuichi; Kato, Keisuke; Fujii, Mikio; Ida, Yoshiteru; Akita, Hiroyuki Tetrahedron, 2006 , vol. 62, # 37 p. 8687 - 8695

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Citation Number: 19

Abstract

Chiral enolate derived from (4R)-4-tert-butyldiphenylsilyloxymethyl-4-butanolide 10 with lithium hexamethyldisilyazide (LiHMDS) was treated with trisyl azide, followed by addition of TMSCl to give (2S, 4R)-2-azido-4-[(tert-butyldiphenylsilyloxy) methyl]-4-butanolide 8 (53%), from which the first total synthesis of polyoxin M (1) was achieved in overall 3.2% yield (13 steps) from d-glutamic acid. Moreover, the synthesis of the reported synthetic intermediate ...