Vinylogous addition of siloxyfurans to benzopyryliums: A concise approach to the tetrahydroxanthone natural products

Tian Qin, Richard P. Johnson, John A. Porco

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

A concise approach to the tetrahydroxanthone natural products employing vinylogous addition of siloxyfurans to benzopyryliums and a late-stage Dieckmann cyclization has been developed. With this methodology, chiral, racemic forms of the natural products blennolides B and blennolide C have been synthesized in a maximum of four steps from a 5-hydroxychromone substrate. The regio- and diastereoselectivity of the vinylogous additions was probed using computational studies, which suggested the involvement of Diels-Alder-like transition states.

Original languageEnglish (US)
Pages (from-to)1714-1717
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number6
DOIs
StatePublished - Feb 16 2011
Externally publishedYes

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Regioselectivity
Cyclization
Biological Products
Substrates
blennolide C

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Vinylogous addition of siloxyfurans to benzopyryliums : A concise approach to the tetrahydroxanthone natural products. / Qin, Tian; Johnson, Richard P.; Porco, John A.

In: Journal of the American Chemical Society, Vol. 133, No. 6, 16.02.2011, p. 1714-1717.

Research output: Contribution to journalArticle

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