Convergent enantioselective synthesis of the tricyclic core of phomactin A

Org Lett. 2002 Jul 11;4(14):2413-6. doi: 10.1021/ol026159t.

Abstract

[reaction: see text] The tricyclic core of phomactin A was synthesized from 6,6-dimethyl-2-cyclohexen-1-one. Key reactions include the addition of a cyclohexenyllithium reagent to an epoxyaldehyde and a regioselective intramolecular epoxide opening to install the oxadecalin core.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Ascomycota / chemistry*
  • Epoxy Compounds / chemistry
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Indicators and Reagents
  • Platelet Activating Factor / antagonists & inhibitors*

Substances

  • Epoxy Compounds
  • Heterocyclic Compounds, 4 or More Rings
  • Indicators and Reagents
  • Platelet Activating Factor
  • phomactin A