Transition-Metal-Free Total Synthesis and Revision of the Absolute Configuration of Pipermethystine

被引：6
|
作者：
Vazquez-Amaya, Laura Y. [1 ]
Quintero, Leticia [1 ]
Rodriguez-Molina, Braulio [2 ]
Sartillo-Piscil, Fernando [1 ]
机构：
[1] BUAP, Fac Ciencias Quim, Ctr Invest, Puebla 72570, Mexico
[2] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 05期
关键词：
1ST TOTAL-SYNTHESIS; KAVA; ENANTIOMERS; ASSIGNMENT;
D O I：
10.1021/acs.joc.9b03218
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Starting from 3-hydroxy piperidines, a novel transition-metal-free strategy to 5-hydroxy-5,6-dihydro-2(1H)pyridones is reported. This unprecedented approach, which provides a practical, economical, and ecofriendly alternative to either the classical ring-closing metathesis of N-homoallyl-unsaturated amides or the dehydrogenation of amides, occurs by means of a triple C-H functionalization of three unreactive piperidine sp(3) carbons. The completion of the total synthesis revealed that the natural levoisomer possesses the R absolute configuration, not S.
引用
收藏
页码：3949 / 3953
页数：5
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