Total synthesis of spirobacillene A

Org Lett. 2013 Jul 5;15(13):3306-9. doi: 10.1021/ol4013958. Epub 2013 Jun 20.

Abstract

The first total synthesis of spirobacillene A, an indole alkaloid isolated from Lysinibacillus fusiformis, is reported. A Lewis acid mediated spirocyclization of an anisole derivative onto a tethered ynone was used as a key step, drawing inspiration from a potential biosynthesis of the natural product.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anisoles / chemistry*
  • Cyclization
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry*
  • Cyclopentanes / isolation & purification
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / isolation & purification
  • Lewis Acids / chemistry*
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry*
  • Spiro Compounds / isolation & purification
  • Stereoisomerism

Substances

  • Anisoles
  • Cyclopentanes
  • Indole Alkaloids
  • Lewis Acids
  • Spiro Compounds
  • spirobacillene A