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

页码：3949 / 3953

页数：5

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