Phorbol Rearrangements

J Nat Prod. 2018 Sep 28;81(9):2134-2137. doi: 10.1021/acs.jnatprod.8b00607. Epub 2018 Sep 14.

Abstract

An alternative procedure for isolation of 4β-phorbol from seeds of Croton tiglium has been developed, and an artifact containing a furan ring formed by rearrangement of 12,13,20- O-triacylated phorbol derivatives into (6b S,7 R,8 R,8a S)-2-(hydroxymethyl)-5,7,9,9-tetramethyl-3,7,8,9,9a,9b-hexahydrocyclopropa[3',4']benzo[1',2':3,4]cyclohepta[1,2- b]furan-6b,8,8a-triol (8a) has been characterized. A mechanism involving an oxidative rearrangement and a decarboxylation for formation of the artifact is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Croton / chemistry*
  • Phorbols / chemistry*
  • Phorbols / isolation & purification
  • Seeds / chemistry

Substances

  • Phorbols