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

Research output: Contribution to journalArticle

18 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)4338-4341
Number of pages4
JournalOrganic Letters
Volume14
Issue number17
DOIs
StatePublished - Sep 7 2012

Fingerprint

Vanadium
Sulfones
sulfones
epoxy compounds
Epoxy Compounds
Biological Products
vanadium
esters
Esters
rings
synthesis
products
Experiments
talaroderxine A
pigmentosin A
talaroderxine B

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Grove, C. I., Di Maso, M. J., Jaipuri, F. A., Kim, M. B., & Shaw, J. T. (2012). Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B. Organic Letters, 14(17), 4338-4341. https://doi.org/10.1021/ol301743t

Synthesis of 6,6′-binaphthopyran-2-one natural products : Pigmentosin A, talaroderxines A and B. / Grove, Charles I.; Di Maso, Michael J.; Jaipuri, Firoz A.; Kim, Michelle B.; Shaw, Jared T.

In: Organic Letters, Vol. 14, No. 17, 07.09.2012, p. 4338-4341.

Research output: Contribution to journalArticle

Grove, CI, Di Maso, MJ, Jaipuri, FA, Kim, MB & Shaw, JT 2012, 'Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B', Organic Letters, vol. 14, no. 17, pp. 4338-4341. https://doi.org/10.1021/ol301743t
Grove, Charles I. ; Di Maso, Michael J. ; Jaipuri, Firoz A. ; Kim, Michelle B. ; Shaw, Jared T. / Synthesis of 6,6′-binaphthopyran-2-one natural products : Pigmentosin A, talaroderxines A and B. In: Organic Letters. 2012 ; Vol. 14, No. 17. pp. 4338-4341.
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