New Strategy for Forging Contiguous Quaternary Carbon Centers via H2O2-Mediated Ring Contraction

Jiadong Hu; Xin Yu; Weiqing Xie

doi:10.1055/s-0036-1590979

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(19): 2517-2524
DOI: 10.1055/s-0036-1590979

synpacts

New Strategy for Forging Contiguous Quaternary Carbon Centers via H₂O₂-Mediated Ring Contraction

Jiadong Hu

^aShaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, P. R. of China eMail: xiewq@nwafu.edu.cn

,

Xin Yu

^bInstrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China

,

Weiqing Xie *

^aShaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, P. R. of China eMail: xiewq@nwafu.edu.cn

^cKey Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling, Shaanxi 712100, P. R. of China

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Abstract

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Abstract

Stereospecific construction of contiguous quaternary carbon centers constitutes a major challenge in natural product synthesis. A general protocol that enables stereospecific construction of all stereoisomers of such a moiety remains elusive. In this article, we will discuss the oxidative ring contraction of all-substituted cyclic α-formyl ketones mediated by H₂O₂, which provides a facile access to the stereospecific construction of contiguous quaternary carbon centers.

Key words

interrupted Baeyer–Villiger reaction - malondialdehyde - cyclic α-formyl ketones - ring contraction - contiguous quaternary carbon centers

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