Highly selective copper-catalyzed ring expansion of vinyl thiiranes: Application to synthesis of biotin and the heterocyclic core of plavix

Erik Rogers; Hiroshi Araki; Lindsay A. Batory; Christine E. McInnis; Jon T. Njardarson

doi:10.1021/ja069059h

Highly selective copper-catalyzed ring expansion of vinyl thiiranes: Application to synthesis of biotin and the heterocyclic core of plavix

Erik Rogers, Hiroshi Araki, Lindsay A. Batory, Christine E. McInnis, Jon T. Njardarson

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

60 Scopus citations

Abstract

We report herein a new, highly selective, mild copper-catalyzed vinyl thiirane ring-expansion protocol for the formation of 2,5-dihydrothiophenes. Preliminary substrate scope and applications of this new synthetic disconnection to the formal racemic total synthesis of biotin and the synthesis of the antiplatelet blockbuster pharmaceutical agent Plavix are described.

Original language	English (US)
Pages (from-to)	2768-2769
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	10
DOIs	https://doi.org/10.1021/ja069059h
State	Published - Mar 14 2007
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja069059h

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abstract = "We report herein a new, highly selective, mild copper-catalyzed vinyl thiirane ring-expansion protocol for the formation of 2,5-dihydrothiophenes. Preliminary substrate scope and applications of this new synthetic disconnection to the formal racemic total synthesis of biotin and the synthesis of the antiplatelet blockbuster pharmaceutical agent Plavix are described.",

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T1 - Highly selective copper-catalyzed ring expansion of vinyl thiiranes

T2 - Application to synthesis of biotin and the heterocyclic core of plavix

AU - Rogers, Erik

AU - Araki, Hiroshi

AU - Batory, Lindsay A.

AU - McInnis, Christine E.

AU - Njardarson, Jon T.

PY - 2007/3/14

Y1 - 2007/3/14

N2 - We report herein a new, highly selective, mild copper-catalyzed vinyl thiirane ring-expansion protocol for the formation of 2,5-dihydrothiophenes. Preliminary substrate scope and applications of this new synthetic disconnection to the formal racemic total synthesis of biotin and the synthesis of the antiplatelet blockbuster pharmaceutical agent Plavix are described.

AB - We report herein a new, highly selective, mild copper-catalyzed vinyl thiirane ring-expansion protocol for the formation of 2,5-dihydrothiophenes. Preliminary substrate scope and applications of this new synthetic disconnection to the formal racemic total synthesis of biotin and the synthesis of the antiplatelet blockbuster pharmaceutical agent Plavix are described.

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Highly selective copper-catalyzed ring expansion of vinyl thiiranes: Application to synthesis of biotin and the heterocyclic core of plavix

Abstract

ASJC Scopus subject areas

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