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

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.

SUBMITTER: Lynch DM

PROVIDER: S-EPMC10367065 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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

Lynch Dylan M DM Nolan Mark D MD Williams Conor C Van Dalsen Leendert L Calvert Susannah H SH Dénès Fabrice F Trujillo Cristina C Scanlan Eoin M EM

The Journal of organic chemistry 20230707 14

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-<i>exo</i>-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. ...[more]

PMID: 37418624

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