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A stereoselective synthesis of (+)-herboxidiene/GEX1A.

ABSTRACT: A stereoselective synthesis of (+)-herboxidiene is described. The convergent synthesis utilized a Suzuki cross-coupling reaction to assemble the key segments. The synthesis of the functionalized tetrahydropyran ring utilized an Achmatowicz reaction as the key step. The synthesis of the C10-C19 segment was accomplished using Brown's crotylboration, asymmetric alkylation, and a stereoselective allylic chlorination reactions.

SUBMITTER: Ghosh AK

PROVIDER: S-EPMC3075843 | biostudies-literature | 2011 Jan

REPOSITORIES: biostudies-literature

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A stereoselective synthesis of (+)-herboxidiene/GEX1A.

Ghosh Arun K AK Li Jianfeng J

Organic letters 20101202 1

A stereoselective synthesis of (+)-herboxidiene is described. The convergent synthesis utilized a Suzuki cross-coupling reaction to assemble the key segments. The synthesis of the functionalized tetrahydropyran ring utilized an Achmatowicz reaction as the key step. The synthesis of the C10-C19 segment was accomplished using Brown's crotylboration, asymmetric alkylation, and a stereoselective allylic chlorination reactions. ...[more]

PMID: 21126066

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