Total Syntheses of (+)??Valiolamine and (–)??1??epi??Valiolamine from Naturally Abundant (–)??Shikimic Acid

N Quan, LD Nie, RH Zhu, XX Shi…

Index: Quan, Na; Nie, Liang-Deng; Zhu, Rui-Heng; Shi, Xiao-Xin; Ding, Wei; Lu, Xia European Journal of Organic Chemistry, 2013 , # 28 p. 6389 - 6396

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Citation Number: 4

Abstract

Abstract Total syntheses of (+)-valiolamine (1) and (–)-1-epi-valiolamine (2) from the naturally abundant (–)-shikimic acid are described. Ethyl 3-epi-5-O-methylsulfonyl-shikimate (3), as the key common intermediate, was first synthesized in five steps in 74% overall yield, and then converted into the targets 1 and 2 in seven steps in 48 and 41% overall yield, respectively.

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