Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum

Org Lett. 2013 Dec 6;15(23):5936-9. doi: 10.1021/ol4027528. Epub 2013 Nov 18.

Abstract

Transformations that selectively modify the furan ring present in a variety of naturals products would be useful in the synthesis of biological probes but remain largely underexplored. The neoclerodane diterpene salvinorin A, isolated from Salvia divinorum, is an example of a furan-containing natural product. Following selective bromination of salvinorin A, Suzuki-Miyaura and Sonogashira couplings were accomplished in moderate to good yields without hydrolyzing the labile C-2 acetate or altering the stereochemistry of the epimerizable centers.

Publication types

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

MeSH terms

  • Biological Products / chemistry*
  • Combinatorial Chemistry Techniques
  • Diterpenes, Clerodane / chemistry*
  • Furans / chemistry
  • Molecular Structure
  • Palladium / chemistry*
  • Salvia / chemistry*

Substances

  • Biological Products
  • Diterpenes, Clerodane
  • Furans
  • Palladium
  • salvinorin A