Enantioselective Synthesis of the ABC-Tricyclic Core of Phomactin A by a γ-Hydroxylation Strategy

Org Lett. 2015 May 1;17(9):2062-5. doi: 10.1021/acs.orglett.5b00586. Epub 2015 Apr 10.

Abstract

An enantioselective synthesis of the ABC-tricyclic furanochroman core of phomactin A has been accomplished by a γ-hydroxylation approach. The C ring was established by γ-hydroxylation of an α-enone. The regioselectivity was optimized by using a strong base with an oxophilic cation (t-BuLi) and a bulky oxygen donor (Davis reagent), which afforded the γ-hydroxylation product selectively in 63% yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascomycota / chemistry
  • Chromans / chemical synthesis
  • Chromans / chemistry
  • Furans / chemical synthesis
  • Furans / chemistry
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Hydroxylation
  • Indicators and Reagents
  • Molecular Structure
  • Stereoisomerism

Substances

  • Chromans
  • Furans
  • Heterocyclic Compounds, 4 or More Rings
  • Indicators and Reagents
  • furanochroman
  • phomactin A