Total Synthesis of (±)-Perophoramidine

James R. Fuchs; Raymond L. Funk

doi:10.1021/ja049569g

Total Synthesis of (±)-Perophoramidine

James R. Fuchs, Raymond L. Funk

Chemistry

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

153 Scopus citations

Abstract

The first total synthesis of racemic perophoramidine is described. The key step features the highly stereoselective introduction of the vicinial quaternary centers via base-promoted carbon-carbon bond formation between a 3-alkylindole and a 3-bromo-3-alkylindolin-2-one. This transformation presumably proceeds through a conjugate addition or Diels-Alder cycloaddition of the 3-alkylindole with a 3-alkylindol-2-one intermediate.

Original language	English (US)
Pages (from-to)	5068-5069
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	126
Issue number	16
DOIs	https://doi.org/10.1021/ja049569g
State	Published - Apr 28 2004

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja049569g

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abstract = "The first total synthesis of racemic perophoramidine is described. The key step features the highly stereoselective introduction of the vicinial quaternary centers via base-promoted carbon-carbon bond formation between a 3-alkylindole and a 3-bromo-3-alkylindolin-2-one. This transformation presumably proceeds through a conjugate addition or Diels-Alder cycloaddition of the 3-alkylindole with a 3-alkylindol-2-one intermediate.",

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AU - Funk, Raymond L.

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AB - The first total synthesis of racemic perophoramidine is described. The key step features the highly stereoselective introduction of the vicinial quaternary centers via base-promoted carbon-carbon bond formation between a 3-alkylindole and a 3-bromo-3-alkylindolin-2-one. This transformation presumably proceeds through a conjugate addition or Diels-Alder cycloaddition of the 3-alkylindole with a 3-alkylindol-2-one intermediate.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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ER -

Total Synthesis of (±)-Perophoramidine

Abstract

All Science Journal Classification (ASJC) codes

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