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

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 stereospecific access to enantiomerically enriched allylated intermediate, offering better prospects for the total synthesis of this natural product.

SUBMITTER: Wierzejska J

PROVIDER: S-EPMC3511019 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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

Wierzejska Jolanta J Motogoe Shin-Ichi S Makino Yuto Y Sengoku Tetsuya T Takahashi Masaki M Yoda Hidemi H

Beilstein journal of organic chemistry 20121025

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 stereospecific access to enantiomerically enriched allylated intermediate, ...[more]

PMID: 23209519

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