Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes

Dylan M. Lynch, Mark D. Nolan, Conor Williams, Leendert Van Dalsen, Susannah H. Calvert, Fabrice Dénès, Cristina Trujillo, Eoin M. Scanlan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Five-membered ring systems are ubiquitous throughout natural products and synthetic therapeutics, and thus, efficient methods to access this essential scaffold are required. Herein, we report the thioacid-mediated, 5-exo-trig cyclization of various 1,6-dienes, with high yields of up to 98%. The labile thioester functionality can be exploited to generate a free thiol residue which can be used as a functional handle or removed entirely to provide the traceless cyclized product.

Original languageEnglish
Pages (from-to)10020-10026
Number of pages7
JournalJournal of Organic Chemistry
Volume88
Issue number14
Early online date7 Jul 2023
DOIs
Publication statusPublished - 21 Jul 2023

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