Three-component coupling approach to trachyspic acid

Org Lett. 2011 Oct 7;13(19):5136-9. doi: 10.1021/ol202002r. Epub 2011 Aug 31.

Abstract

Three-component coupling of the lithium enolate of t-BuOAc, silyl glyoxylate, and an α,β-unsaturated ketone enables the rapid construction of the trachyspic acid carbon skeleton. A 3,4-disubstituted isoxazole is utilized to mask the C7/C9 dicarbonyl. New enolsilane/nitrile-oxide cycloadditions enable the preparation of various 3,4-disubstituted isoxazoles that are challenging to access by other means.

Publication types

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

MeSH terms

  • Isoxazoles / chemistry
  • Molecular Structure
  • Nitriles / chemistry
  • Oxides / chemistry
  • Spiro Compounds / chemistry*

Substances

  • Isoxazoles
  • Nitriles
  • Oxides
  • Spiro Compounds
  • trachyspic acid