Total synthesis of (±)-7-epi-nemorosone

Org Lett. 2012 Apr 6;14(7):1796-9. doi: 10.1021/ol300386t. Epub 2012 Mar 26.

Abstract

A concise total synthesis of (±)-7-epi-nemorosone is reported. Our synthetic approach establishes a viable route to polycyclic polyprenylated acylphloroglucinol natural products (PPAP's) bearing a C-7 endo prenyl side chain. Key steps include retro-aldol-vinyl cerium addition to a hydroxy adamantane core scaffold and palladium-mediated deoxygenation.

Publication types

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

MeSH terms

  • Benzophenones / chemical synthesis*
  • Benzophenones / chemistry
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Cyclization
  • Molecular Structure
  • Stereoisomerism

Substances

  • Benzophenones
  • Biological Products
  • nemorosone