Chengying Zhou, Weitian Qin, Canhui Tu, Yunxuan Chen, Shaomin Fu, Bo Liu
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引用次数: 0
Abstract
Euphane triterpenoids are widely distributed in nature and show various intriguing bioactivities, but relatively few synthetic routes to them have been described. Here we report asymmetric convergent total syntheses of euphanes involving two triterpenoids and two nortriterpenoids: euphol, 25,26,27-trisnor-3β-hydroxy-euphan-24-al, euphorbiumrin D and oxo-tirucall-7-ene-3,20-dione. The syntheses employ an enantioselective Antilla allylboration and intramolecular radical cyclization to construct ring A, a palladium-catalyzed Liebeskind stannane-thioester coupling to connect ring A with the bicyclic CD system, and a novel radical cascade with metal-catalyzed hydrogen atom transfer (MHAT) to complete the polycyclic architecture. The late-stage syntheses of both triterpenoids feature a diimide reduction and a MHAT/1,5-hydrogen transfer cascade to diastereoselectively forge the C20 and C17 stereogenic centers.
期刊介绍:
Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.