Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B

Charles I. Grove; Michael J. Di Maso; Firoz A. Jaipuri; Michelle B. Kim; Jared T. Shaw

doi:10.1021/ol301743t

Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B

Charles I. Grove, Michael J. Di Maso, Firoz A. Jaipuri, Michelle B. Kim, Jared T. Shaw

Chemistry

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

21 Scopus citations

Abstract

Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.

Original language	English (US)
Pages (from-to)	4338-4341
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	17
DOIs	https://doi.org/10.1021/ol301743t
State	Published - Sep 7 2012

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

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title = "Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B",

abstract = "Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.",

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AU - Grove, Charles I.

AU - Di Maso, Michael J.

AU - Jaipuri, Firoz A.

AU - Kim, Michelle B.

AU - Shaw, Jared T.

PY - 2012/9/7

Y1 - 2012/9/7

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AB - Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.

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Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B

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