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Total synthesis of the proposed structure of briarellin J.

ABSTRACT: The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC2966518 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Total synthesis of the proposed structure of briarellin J.

Crimmins Michael T MT Mans Mark C MC Rodríguez Abimael D AD

Organic letters 20101101 21

The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure. ...[more]

PMID: 20936859

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