Evolution of a synthetic strategy: Total synthesis of (±)- welwitindolinone A isonitrile

Sarah E. Reisman; Joseph M. Ready; Matthew M. Weiss; Atsushi Hasuoka; Makoto Hirata; Kazuhiko Tamaki; Timo V. Ovaska; Catherine J. Smith; John L. Wood

doi:10.1021/ja076663z

Evolution of a synthetic strategy: Total synthesis of (±)- welwitindolinone A isonitrile

Sarah E. Reisman, Joseph M. Ready, Matthew M. Weiss, Atsushi Hasuoka, Makoto Hirata, Kazuhiko Tamaki, Timo V. Ovaska, Catherine J. Smith, John L. Wood

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

142 Scopus citations

Abstract

An efficient and highly stereoselective total synthesis of the natural product (±)-welwitindolinone A isonitrile (1) is described. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with excellent stereocontrol via a chloronium ion mediated semipinacol rearrangement. Described strategies for construction of the spiro-oxinole include a Sml ₂-LiCl mediated reductive cyclization and a novel anionic cyclization that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.

Original language	English (US)
Pages (from-to)	2087-2100
Number of pages	14
Journal	Journal of the American Chemical Society
Volume	130
Issue number	6
DOIs	https://doi.org/10.1021/ja076663z
State	Published - Feb 13 2008

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Evolution of a synthetic strategy: Total synthesis of (±)- welwitindolinone A isonitrile",

abstract = "An efficient and highly stereoselective total synthesis of the natural product (±)-welwitindolinone A isonitrile (1) is described. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with excellent stereocontrol via a chloronium ion mediated semipinacol rearrangement. Described strategies for construction of the spiro-oxinole include a Sml 2-LiCl mediated reductive cyclization and a novel anionic cyclization that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.",

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T1 - Evolution of a synthetic strategy

T2 - Total synthesis of (±)- welwitindolinone A isonitrile

AU - Reisman, Sarah E.

AU - Ready, Joseph M.

AU - Weiss, Matthew M.

AU - Hasuoka, Atsushi

AU - Hirata, Makoto

AU - Tamaki, Kazuhiko

AU - Ovaska, Timo V.

AU - Smith, Catherine J.

AU - Wood, John L.

PY - 2008/2/13

Y1 - 2008/2/13

N2 - An efficient and highly stereoselective total synthesis of the natural product (±)-welwitindolinone A isonitrile (1) is described. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with excellent stereocontrol via a chloronium ion mediated semipinacol rearrangement. Described strategies for construction of the spiro-oxinole include a Sml 2-LiCl mediated reductive cyclization and a novel anionic cyclization that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.

AB - An efficient and highly stereoselective total synthesis of the natural product (±)-welwitindolinone A isonitrile (1) is described. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with excellent stereocontrol via a chloronium ion mediated semipinacol rearrangement. Described strategies for construction of the spiro-oxinole include a Sml 2-LiCl mediated reductive cyclization and a novel anionic cyclization that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.

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Evolution of a synthetic strategy: Total synthesis of (±)- welwitindolinone A isonitrile

Abstract

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