Convergent route to the spirohexenolide macrocycle

Org Lett. 2010 Oct 15;12(20):4516-9. doi: 10.1021/ol1018163.

Abstract

Using key functional dissections, the synthesis of spirohexenolides is examined through a three-component strategy that features a 1,2-addition to couple tetronate and aldehyde components forming the C2-C3 bond and a Stille coupling to install the third sulfone-containing component. The macrocycle is completed by an intramolecular Julia-Kocienski reaction to form the C10-C11 trans-disubstituted olefin. Application of this strategy is described in progress toward the synthesis of (±)-spirohexenolide B.

Publication types

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

MeSH terms

  • Models, Molecular
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*

Substances

  • Spiro Compounds