Construction of epidithiodioxopiperazines by directed oxidation of hydroxyproline-derived dioxopiperazines

Larry E. Overman; Takaaki Sato

doi:10.1021/ol702518t

Construction of epidithiodioxopiperazines by directed oxidation of hydroxyproline-derived dioxopiperazines

Larry E. Overman, Takaaki Sato

Research output: Contribution to journal › Article › peer-review

45 Citations (Scopus)

Abstract

(Chemical Equation Presented) Functionalization of the angular methine carbon of hydroxyproline-derived dioxopiperazines by a radical-promoted C-H bond oxidation, which is directed by a proximal (bromomethyl)silyl group, is described. This regioselective oxidation is the key step in a new synthesis of epidithiodioxopiperazines.

Original language	English
Pages (from-to)	5267-5270
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	25
DOIs	https://doi.org/10.1021/ol702518t
Publication status	Published - 2007 Dec 6
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Chemical Equation Presented) Functionalization of the angular methine carbon of hydroxyproline-derived dioxopiperazines by a radical-promoted C-H bond oxidation, which is directed by a proximal (bromomethyl)silyl group, is described. This regioselective oxidation is the key step in a new synthesis of epidithiodioxopiperazines.",

author = "Overman, {Larry E.} and Takaaki Sato",

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N2 - (Chemical Equation Presented) Functionalization of the angular methine carbon of hydroxyproline-derived dioxopiperazines by a radical-promoted C-H bond oxidation, which is directed by a proximal (bromomethyl)silyl group, is described. This regioselective oxidation is the key step in a new synthesis of epidithiodioxopiperazines.

AB - (Chemical Equation Presented) Functionalization of the angular methine carbon of hydroxyproline-derived dioxopiperazines by a radical-promoted C-H bond oxidation, which is directed by a proximal (bromomethyl)silyl group, is described. This regioselective oxidation is the key step in a new synthesis of epidithiodioxopiperazines.

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Construction of epidithiodioxopiperazines by directed oxidation of hydroxyproline-derived dioxopiperazines

Abstract

ASJC Scopus subject areas

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