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

Autor: McGinnis TM; Department of Chemistry, University of California, Irvine, California 92697, United States., Thane TA; Department of Chemistry, University of California, Irvine, California 92697, United States., Jarvo ER; Department of Chemistry, University of California, Irvine, California 92697, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2022 Aug 05; Vol. 24 (30), pp. 5619-5623. Date of Electronic Publication: 2022 Jul 22.
DOI: 10.1021/acs.orglett.2c02362
Abstrakt: 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.
Databáze: MEDLINE