Cyclopropanations of olefin-containing natural products for simultaneous arming and structure activity studies

Org Lett. 2012 Mar 16;14(6):1394-7. doi: 10.1021/ol300105q. Epub 2012 Feb 24.

Abstract

Cyclopropanations of alkene-containing natural products that proceed under mild conditions are reported for simultaneous arming and structure-activity relationship studies. An alkynyl diazo ester under Rh(II) catalysis is employed for cyclopropanations of electron-rich olefins while an alkynyl sulfonium ylide is used for electron-poor olefins. This approach enables simultaneous natural product derivatization for SAR studies and arming (i.e., via alkyne attachment) for subsequent conjugation with reporter tags (e.g., biotin, fluorophores, photoaffinity labels) for mechanism of action studies including cellular target identification and proteome profiling experiments.

Publication types

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

MeSH terms

  • Alkenes / chemistry*
  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Biological Products / chemistry*
  • Catalysis
  • Cyclopropanes / chemistry*
  • Esters
  • Imines
  • Molecular Structure
  • Rhodiola / chemistry
  • Structure-Activity Relationship

Substances

  • Alkenes
  • Alkynes
  • Biological Products
  • Cyclopropanes
  • Esters
  • Imines