A new approach toward the total synthesis of (+)-batzellaside B

J Wierzejska, S Motogoe, Y Makino…

Index: Wierzejska, Jolanta; Motogoe, Shin-Ichi; Makino, Yuto; Sengoku, Tetsuya; Takahashi, Masaki; Yoda, Hidemi Beilstein Journal of Organic Chemistry, 2012 , vol. 8, p. 1831 - 1838,8

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Citation Number: 4

Abstract

Abstract A new synthetic approach to (+)-batzellaside B from naturally abundant L- pyroglutamic acid is presented in this article. The key synthetic step involves Sharpless asymmetric dihydroxylation of an olefinic substrate functionalized with an acetoxy group to introduce two chiral centres diastereoselectively into the structure. Heterocyclic hemiaminal 4, which could be converted from the resulting product, was found to provide ...

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