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Zinc-Mediated Transformation of 1,3-Diols to Cyclopropanes for Late-Stage Modification of Natural Products and Medicinal Agents.

ABSTRACT: A method for incorporating cyclopropane motifs into complex molecules has been developed. Herein we report a zinc dust-mediated cross-electrophile coupling reaction of 1,3-dimesylates to synthesize cyclopropanes. 1,3-Dimesylates can be readily accessed from 1,3-diols, a functionality prevalent in many natural products and medicinal agents. The reaction conditions are mild, such that functional groups, including amides, esters, heterocycles, and alkenes, are tolerated. Notably, we have demonstrated late-stage cyclopropanation of statin medicinal agents.

SUBMITTER: McGinnis TM

PROVIDER: S-EPMC9361355 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Zinc-Mediated Transformation of 1,3-Diols to Cyclopropanes for Late-Stage Modification of Natural Products and Medicinal Agents.

McGinnis Tristan M TM Thane Taylor A TA Jarvo Elizabeth R ER

Organic letters 20220722 30

A method for incorporating cyclopropane motifs into complex molecules has been developed. Herein we report a zinc dust-mediated cross-electrophile coupling reaction of 1,3-dimesylates to synthesize cyclopropanes. 1,3-Dimesylates can be readily accessed from 1,3-diols, a functionality prevalent in many natural products and medicinal agents. The reaction conditions are mild, such that functional groups, including amides, esters, heterocycles, and alkenes, are tolerated. Notably, we have demonstrat ...[more]

PMID: 35867876

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