Intramolecular allenolate acylations in studies toward a synthesis of FR182877

Christopher D. Vanderwal, David A. Vosburg, Erik J. Sorensen

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(Matrix Presented) During our efforts to synthesize the cytotoxic natural product FR182877, we discovered intramolecular reductive acylations that offer a stereocontrolled alternative to the classical Knoevenagel condensation for the formation of α-alkylidene β-keto-δ-lactones. Other progress toward a synthesis of FR182877 includes a π-allyl Stille coupling and a bromo Horner-Wadsworth-Emmons reaction that forms a 12-membered ring. Structural relationships among FR182877, hexacyclinic acid, macquarimicin A, and cochleamycin A are also discussed.

Original languageEnglish (US)
Pages (from-to)4307-4310
Number of pages4
JournalOrganic letters
Issue number26
StatePublished - Dec 27 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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