Studies toward the total synthesis of popolohuanone E: enantioselective synthesis of 8-O-methylpopolohuanone E

Org Lett. 2001 Aug 23;3(17):2701-4. doi: 10.1021/ol016285h.

Abstract

[structure: see text]. 8-O-methylpopolohuanone E (2) was synthesized in a highly convergent manner starting from the cis-fused decalin derivative accessible from the (-)-Wieland-Miescher ketone analogue. The synthetic method features a biogenetic-type annulation of the phenolic and quinone segments to regioselectively construct the central tricyclic ring system as the key step.

MeSH terms

  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Magnetic Resonance Spectroscopy
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Stereoisomerism
  • Topoisomerase II Inhibitors

Substances

  • 8-O-methylpopolohuanone E
  • Enzyme Inhibitors
  • Sesquiterpenes
  • Topoisomerase II Inhibitors