Total synthesis of irciniastatin A (Psymberin)

Org Lett. 2009 Sep 3;11(17):3990-3. doi: 10.1021/ol901655e.

Abstract

The total synthesis of (+)-iriciniastatin A (psymberin) is reported in 19 steps and 6% overall yield. Key reactions include a highly convergent enolsilane-oxocarbenium ion union to generate the C8-C25 fragment and a late-stage coupling of a hemiaminal and acid chloride to complete the synthesis.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Catalysis
  • Coumarins
  • Molecular Structure
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Stereoisomerism

Substances

  • Coumarins
  • Pyrones
  • psymberin