Total Syntheses of Cinchona Alkaloids via Photoredox-Catalyzed Deoxygenative Arylation

被引：8
|
作者：
Li, Lei [1 ,2 ]
Yang, Hua-Fei [1 ,2 ]
Ding, Qian-Hui [1 ,2 ]
Wei, Kun [1 ]
Yang, Yu-Rong [1 ]
机构：
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Chi, Kunming 650201, Peoples R China
[2] Univ Chinese Acad Sci, Beijing, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 24期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC TOTAL SYNTHESES; ALPHA-ALLYLATION; FORMAL SYNTHESIS; QUININE;
D O I：
10.1021/acs.orglett.3c01659
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Metallaphotoredox-enableddeoxygenative arylation of alcohols isa recently developed robust synthetic strategy for sp(2)-sp(3) coupling by MacMillan. Inspired by this method, we reportherein its first utilization in natural product total synthesis throughrealizing the coupling of 4-bromo-quinoline or 4-bromo-6-methoxyquinolinewith quincorine or quincoridine, respectively. The alcohols were denovo synthesized in racemic form by a key step of the intramolecularDiels-Alder reaction or in an enantioselective manner by Ir/aminedual-catalyzed allylation. All members of the cinchona alkaloids couldbe prepared efficiently.
引用
收藏
页码：4586 / 4591
页数：6
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