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Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization-Cross-Coupling Cascade.

ABSTRACT: An alkoxycarbonyl radical cyclization-cross-coupling cascade has been developed that allows functionalized ?-butyrolactones to be prepared in one step from simple tertiary alcohol-derived homoallylic oxalate precursors. The reaction succeeds with aryl and vinyl electrophiles and is compatible with heterocyclic fragments in both coupling partners. This chemistry allows for the rapid construction of spirolactones, which are of interest in drug discovery endeavors.

SUBMITTER: Weires NA

PROVIDER: S-EPMC6555670 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization-Cross-Coupling Cascade.

Weires Nicholas A NA Slutskyy Yuriy Y Overman Larry E LE

Angewandte Chemie (International ed. in English) 20190513 25

An alkoxycarbonyl radical cyclization-cross-coupling cascade has been developed that allows functionalized γ-butyrolactones to be prepared in one step from simple tertiary alcohol-derived homoallylic oxalate precursors. The reaction succeeds with aryl and vinyl electrophiles and is compatible with heterocyclic fragments in both coupling partners. This chemistry allows for the rapid construction of spirolactones, which are of interest in drug discovery endeavors. ...[more]

PMID: 30989757

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