Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization

Chambers C. Hughes, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Sidestepping stereochemical inversion: In an expedient, asymmetric total synthesis of (-)-frondosin B a novel palladium-catalyzed cyclization establishes the tetracyclic skeleton (see scheme). The absolute stereochemistry of naturally occurring marine metabolite (+)-frondosin B, an interleukin-8 inhibitor, has been reassigned. Tf = trifluoromethanesulfonyl.

Original languageEnglish (US)
Pages (from-to)1569-1572
Number of pages4
JournalAngewandte Chemie - International Edition
Volume41
Issue number9
DOIs
StatePublished - May 3 2002

Fingerprint

Cyclization
Palladium
Stereochemistry
Metabolites
Interleukin-8
frondosin B

Keywords

  • Cyclization
  • Natural products
  • Palladium
  • Polycycles
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization. / Hughes, Chambers C.; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 41, No. 9, 03.05.2002, p. 1569-1572.

Research output: Contribution to journalArticle

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