A rapid, asymmetric synthesis of the decahydrofluorene core of the hirsutellones

S. David Tilley, Keith P. Reber, Erik J. Sorensen

Research output: Contribution to journalArticle

41 Scopus citations

Abstract

(Chemical Equation Presented) A tandem ketene-trapping/Diels-Alder cyclization sequence was the pivotal transformation in an efficient, asymmetric synthesis of a decahydrofluorene tricyclic structure possessing eight stereogenic centers and key features of the hirsutellone class of antitubercular natural products. The hirsutellone-like β-keto ester that was fashioned by this sequence (13 steps; 6% overall yield) demonstrated significant inhibitory activity against Mycobacterium tuberculosis. The mechanism of action of this antitubercular compound is not yet known.

Original languageEnglish (US)
Pages (from-to)701-703
Number of pages3
JournalOrganic letters
Volume11
Issue number3
DOIs
StatePublished - Feb 5 2009

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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