NOC approach to spiroketals. A total synthesis of (±)-talaromycin B

Alan P. Kozikowski, James G. Scripko

Research output: Contribution to journalArticle

Abstract

A total synthesis of the unqiue spiroketal natural product talaromycin B (1) is reported. This molecule, produced in nature by the toxicogenic fungus Talaromyces stipitatus, was constructed in the laboratory from the isoxazoline 6 generated (Chemical Equation Presented) on reacting the oxime 4 with the olefin 5 in the presence of NaOCl/Et3N/H2O/CH2Cl2. The synthesis scheme is sufficiently flexible and efficient so as to be of practical use in the preparation of suitable quantities of this material for biological evaluation.

Original languageEnglish (US)
Pages (from-to)353-355
Number of pages3
JournalJournal of the American Chemical Society
Volume106
Issue number2
StatePublished - 1984
Externally publishedYes

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Talaromyces
Oximes
Alkenes
Biological Products
Fungi
Olefins
Molecules
spiroketal
talaromycin B

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

NOC approach to spiroketals. A total synthesis of (±)-talaromycin B. / Kozikowski, Alan P.; Scripko, James G.

In: Journal of the American Chemical Society, Vol. 106, No. 2, 1984, p. 353-355.

Research output: Contribution to journalArticle

Kozikowski, Alan P. ; Scripko, James G. / NOC approach to spiroketals. A total synthesis of (±)-talaromycin B. In: Journal of the American Chemical Society. 1984 ; Vol. 106, No. 2. pp. 353-355.
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