Total synthesis of (±)-welwitindolinone A isonitrile

Sarah E. Reisman; Joseph M. Ready; Atsushi Hasuoka; Catherine J. Smith; John L. Wood

doi:10.1021/ja057640s

Total synthesis of (±)-welwitindolinone A isonitrile

Sarah E. Reisman, Joseph M. Ready, Atsushi Hasuoka, Catherine J. Smith, John L. Wood

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

126 Scopus citations

Abstract

A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol.

Original language	English (US)
Pages (from-to)	1448-1449
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	5
DOIs	https://doi.org/10.1021/ja057640s
State	Published - Feb 8 2006

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja057640s

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title = "Total synthesis of (±)-welwitindolinone A isonitrile",

abstract = "A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol.",

author = "Reisman, {Sarah E.} and Ready, {Joseph M.} and Atsushi Hasuoka and Smith, {Catherine J.} and Wood, {John L.}",

year = "2006",

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T1 - Total synthesis of (±)-welwitindolinone A isonitrile

AU - Reisman, Sarah E.

AU - Ready, Joseph M.

AU - Hasuoka, Atsushi

AU - Smith, Catherine J.

AU - Wood, John L.

PY - 2006/2/8

Y1 - 2006/2/8

N2 - A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol.

AB - A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol.

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Total synthesis of (±)-welwitindolinone A isonitrile

Abstract

ASJC Scopus subject areas

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