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Re₂ O₇ -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

ABSTRACT: Re₂ O₇ catalysis effects efficient and stereoselective dehydrative cyclization reactions from monoallylic diols, with stereocontrol arising from thermodynamic equilibration. This method was applied to a rapid synthesis of the spliceosome inhibitor herboxidiene. The route was also utilized for the synthesis of an analogue that highlights the importance of a single methyl group in biasing the conformation in the acyclic region of the molecule.

SUBMITTER: Rohrs TM

PROVIDER: S-EPMC5687070 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

Rohrs Tyler M TM Qin Qi Q Floreancig Paul E PE

Angewandte Chemie (International ed. in English) 20170728 36

Re2 O7 catalysis effects efficient and stereoselective dehydrative cyclization reactions from monoallylic diols, with stereocontrol arising from thermodynamic equilibration. This method was applied to a rapid synthesis of the spliceosome inhibitor herboxidiene. The route was also utilized for the synthesis of an analogue that highlights the importance of a single methyl group in biasing the conformation in the acyclic region of the molecule. ...[more]

PMID: 28686815

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