Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: confirmation of the relative stereochemistry

Org Biomol Chem. 2012 Mar 7;10(9):1743-5. doi: 10.1039/c2ob06906g. Epub 2012 Jan 24.

Abstract

The stereoselective reaction of an allyl bromide with an aldehyde mediated by a low valency bismuth species was the key reaction in stereoselective syntheses of (4S,6R,8R,10S,16S)- and (4S,6R,8R,10S,16R)-4,6,8,10,16-pentamethyldocosanes. (13)C NMR data for these compounds confirmed that the cuticular hydrocarbon isolated from the cane beetle Antitrogus parvulus was the (4S,6R,8R,10S,16S)-stereoisomer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Coleoptera / anatomy & histology
  • Coleoptera / chemistry*
  • Hydrocarbons / chemical synthesis*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Hydrocarbons