Formal total synthesis of okadaic acid via regiocontrolled gold(I)-catalyzed spiroketalizations

Org Lett. 2010 Oct 15;12(20):4528-31. doi: 10.1021/ol101833h.

Abstract

Both C19 and C34 spiroketal domains of okadaic acid were assembled using gold(I) chloride catalyzed spiroketalizations, and the two resulting fragments were coupled to give the C15-C38 fragment of okadaic acid, a known intermediate for the total synthesis of this important natural product.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Furans / chemistry*
  • Gold / chemistry*
  • Molecular Structure
  • Okadaic Acid / chemical synthesis*
  • Spiro Compounds / chemistry*

Substances

  • Furans
  • Spiro Compounds
  • spiroketal
  • Okadaic Acid
  • Gold