Direct Catalytic Asymmetric Conjugate Addition of Benzofuran-3(2H)-Ones to α,β-Unsaturated Thioamides: Stereodivergent Synthesis of Rocaglaol.

Autor: Samanta S; Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki Shinagawa-ku, Tokyo, 141-0021, Japan., Noda H; Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki Shinagawa-ku, Tokyo, 141-0021, Japan., Watanabe T; Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki Shinagawa-ku, Tokyo, 141-0021, Japan., Cui J; Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki Shinagawa-ku, Tokyo, 141-0021, Japan.; Center for Innovative Drug Discovery, Greater Bay Area Institute of Precision Medicine (Guangzhou), School of Pharmacy, Fudan University, Shanghai, P. R. China., Shibasaki M; Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki Shinagawa-ku, Tokyo, 141-0021, Japan.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Oct 01, pp. e202415805. Date of Electronic Publication: 2024 Oct 01.
DOI: 10.1002/anie.202415805
Abstrakt: Rocaglaol, a representative flavagline, has attracted significant attention because of its unique chemical structure and biological activities. This paper reports a mild and scalable copper-catalyzed enantioselective conjugate addition of benzofuran-3(2H)-ones to α,β-unsaturated thioamides. This method allows for the concise synthesis of all possible stereoisomers of a key intermediate of rocaglaol and its derivatives in a highly diastereo- and enantioselective manner using different chiral phosphine ligands. Theoretical insights into the reaction mechanism and the origin of ligand-dependent diastereodivergence were obtained using density functional theory calculations.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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