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A C–H Functionalization Strategy Enables an Enantioselective Formal Synthesis of (−)-Aflatoxin B2
Organic Letters ( IF 5.2 ) Pub Date : 2021-12-05 , DOI: 10.1021/acs.orglett.1c03502
Nicholas A Falcone 1 , Aaron T Bosse 2 , Hojoon Park 3 , Jin-Quan Yu 3 , Huw M L Davies 2 , Erik J Sorensen 1
Affiliation  

An enantioselective formal synthesis of (−)-aflatoxin B2 from 4-methoxyphenylacetic acid has been achieved by an approach that produces a key carbon–carbon bond, a benzylic stereocenter, and two arene carbon–oxygen bonds in the course of three site-selective C–H functionalizations. The carbonyl-directed acetoxylation of two arene C–H bonds described herein is unprecedented in natural product synthesis and occurs under mild conditions that preserve the configuration of a sensitive benzylic stereocenter.

中文翻译:

AC-H 功能化策略实现了 (-)-黄曲霉毒素 B2 的对映选择性形式合成

通过在三个位点的过程中产生一个关键的碳-碳键、一个苄基立体中心和两个芳烃碳-氧键的方法,已经实现了从 4-甲氧基苯乙酸对 (-)-黄曲霉毒素 B 2的对映选择性正式合成。选择性 C-H 官能化。本文所述的两个芳烃 C-H 键的羰基定向乙酰氧基化在天然产物合成中是前所未有的,并且在保持敏感苄基立体中心构型的温和条件下发生。
更新日期:2021-12-17
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