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

[Image: see text] 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 functionali...

Descripción completa

Detalles Bibliográficos
Autores principales: McGinnis, Tristan M., Thane, Taylor A., Jarvo, Elizabeth R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9361355/
https://www.ncbi.nlm.nih.gov/pubmed/35867876
http://dx.doi.org/10.1021/acs.orglett.2c02362
_version_ 1784764515196338176
author McGinnis, Tristan M.
Thane, Taylor A.
Jarvo, Elizabeth R.
author_facet McGinnis, Tristan M.
Thane, Taylor A.
Jarvo, Elizabeth R.
author_sort McGinnis, Tristan M.
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-9361355
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-93613552022-08-10 Zinc-Mediated Transformation of 1,3-Diols to Cyclopropanes for Late-Stage Modification of Natural Products and Medicinal Agents McGinnis, Tristan M. Thane, Taylor A. Jarvo, Elizabeth R. Org Lett [Image: see text] 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. American Chemical Society 2022-07-22 2022-08-05 /pmc/articles/PMC9361355/ /pubmed/35867876 http://dx.doi.org/10.1021/acs.orglett.2c02362 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle McGinnis, Tristan M.
Thane, Taylor A.
Jarvo, Elizabeth R.
Zinc-Mediated Transformation of 1,3-Diols to Cyclopropanes for Late-Stage Modification of Natural Products and Medicinal Agents
title Zinc-Mediated Transformation of 1,3-Diols to Cyclopropanes for Late-Stage Modification of Natural Products and Medicinal Agents
title_full Zinc-Mediated Transformation of 1,3-Diols to Cyclopropanes for Late-Stage Modification of Natural Products and Medicinal Agents
title_fullStr Zinc-Mediated Transformation of 1,3-Diols to Cyclopropanes for Late-Stage Modification of Natural Products and Medicinal Agents
title_full_unstemmed Zinc-Mediated Transformation of 1,3-Diols to Cyclopropanes for Late-Stage Modification of Natural Products and Medicinal Agents
title_short Zinc-Mediated Transformation of 1,3-Diols to Cyclopropanes for Late-Stage Modification of Natural Products and Medicinal Agents
title_sort zinc-mediated transformation of 1,3-diols to cyclopropanes for late-stage modification of natural products and medicinal agents
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9361355/
https://www.ncbi.nlm.nih.gov/pubmed/35867876
http://dx.doi.org/10.1021/acs.orglett.2c02362
work_keys_str_mv AT mcginnistristanm zincmediatedtransformationof13diolstocyclopropanesforlatestagemodificationofnaturalproductsandmedicinalagents
AT thanetaylora zincmediatedtransformationof13diolstocyclopropanesforlatestagemodificationofnaturalproductsandmedicinalagents
AT jarvoelizabethr zincmediatedtransformationof13diolstocyclopropanesforlatestagemodificationofnaturalproductsandmedicinalagents

Ejemplares similares