Bioinspired synthesis of hirsutellones A, B, and C

Org Lett. 2011 Oct 21;13(20):5708-10. doi: 10.1021/ol202239u. Epub 2011 Sep 14.

Abstract

The total synthesis of hirsutellones A (1), B (2), and C (3) has been achieved through a bioinspired late-stage sequence starting from advanced intermediate 6. The sequence proceeded via labile intermediate 17,1'-dehydrohirsutellone B (5) and delivered, in addition to the natural products (1-3), hirsutellone analogue 1',2',17-epi-hirsutellone C (1',2',17-epi-3).

Publication types

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

MeSH terms

  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Trichoderma / chemistry

Substances

  • Heterocyclic Compounds, 4 or More Rings
  • hirsutellone A
  • hirsutellone B
  • hirsutellone C