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Gamma-spiroketal gamma-lactones from 2-(gamma-hydroxyalkyl)furans: syntheses of epi-pyrenolide D and crassalactone D.

Abstract
Photooxygenation of 2-(gamma-hydroxyalkyl)furans followed by dehydration affords, in one synthetic operation and in high yield, gamma-spiroketal gamma-lactones. This newly developed technology was successfully applied to the synthesis of three different epimers of pyrenolide D, as well as to the first synthesis of the anticancer natural product crassalactone D and its C4-epimer.
AuthorsElias Pavlakos, Thomas Georgiou, Maria Tofi, Tamsyn Montagnon, Georgios Vassilikogiannakis
JournalOrganic letters (Org Lett) Vol. 11 Issue 20 Pg. 4556-9 (Oct 15 2009) ISSN: 1523-7052 [Electronic] United States
PMID19746914 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Furans
  • Hydroxides
  • Lactones
  • Spiro Compounds
  • crassalactone D
  • pyrenolide D
  • spiroketal
  • hydroxide ion
  • Hydrogen Peroxide
Topics
  • Furans (chemical synthesis, chemistry)
  • Hydrogen Peroxide (chemistry)
  • Hydroxides (chemistry)
  • Lactones (chemistry)
  • Spiro Compounds (chemical synthesis, chemistry)

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