Synthesis of cordiaquinones B, C, J, and K on the basis of a bioinspired approach and the revision of the relative stereochemistry of cordiaquinone C

J Org Chem. 2008 Jun 20;73(12):4484-90. doi: 10.1021/jo800355y. Epub 2008 May 23.

Abstract

Four members of the cordiaquinone family (cordiaquinones B, C, J, and K) were synthesized on the basis of a bioinspired scenario in five to six steps from trans, trans-farnesol. As key reactions we used the acid-catalyzed cyclization of a suitable epoxy terpenoid and a Diels-Alder reaction between a diene and benzoquinone. The relative stereochemistry of cordiaquinone C is opposite to that reported in the isolation paper and is in agreement with a plausible scenario for the biosynthesis of cordiaquinones from a common (E)-configurated naphthoquinone epoxide precursor. A fast and clean methodology for the synthesis of the naturally occurring (Z)-beta-farnesene from cis-nerolidol is also reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Magnetic Resonance Spectroscopy
  • Quinones / chemical synthesis*
  • Quinones / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism

Substances

  • Quinones