Synthesis of the C1-C17 segment of phorboxazole B

Org Lett. 2004 Aug 19;6(17):2965-8. doi: 10.1021/ol0488800.

Abstract

The C1-C17 bis-oxane subunit 22 of phorboxazole B is efficiently synthesized by exploiting differential reactivities between similar substituents on the hydropyran rings in 4. Selective dihydroxylation of the equatorial vinyl group, hydroboration of the axial vinyl group, and intramolecular Mitsunobu lactonization serve to fully differentiate the similar hydropyrans.

Publication types

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

MeSH terms

  • Catalysis
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry*
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry

Substances

  • Heterocyclic Compounds, 4 or More Rings
  • Indicators and Reagents
  • Oxazoles
  • Pyrans
  • phorboxazole A