TY - JOUR
T1 - Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes
AU - Lynch, Dylan M.
AU - Nolan, Mark D.
AU - Williams, Conor
AU - Van Dalsen, Leendert
AU - Calvert, Susannah H.
AU - Dénès, Fabrice
AU - Trujillo, Cristina
AU - Scanlan, Eoin M.
N1 - Funding Information:
This work was supported by SSPC, The SFI Research Center for Pharmaceuticals, Grant No. 12/RC/2275_p2 (MN) and (EMS), and SFI 19/FFP/6667 (EMS).
Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society.
PY - 2023/7/21
Y1 - 2023/7/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85165717786&partnerID=8YFLogxK
UR - https://www.mendeley.com/catalogue/5febcf89-7464-3498-9dba-83b144ca3a58/
U2 - 10.1021/acs.joc.3c00824
DO - 10.1021/acs.joc.3c00824
M3 - Article
AN - SCOPUS:85165717786
SN - 0022-3263
VL - 88
SP - 10020
EP - 10026
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 14
ER -