Total synthesis of (+)-gregatin B and E

Org Lett. 2013 Oct 4;15(19):5102-5. doi: 10.1021/ol402472q. Epub 2013 Sep 25.

Abstract

The first total synthesis of (+)-gregatin E and a new total synthesis of (+)-gregatin B are described. Key features of our synthetic approach involve a palladium-catalyzed cyclization-methoxycarbonylation of optically active propargylic acetate and a Suzuki-Miyaura coupling or CuTC-mediated coupling reaction. The absolute configuration of (+)-gregatin E (5R,5'S) is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Catalysis
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Molecular Structure
  • Palladium / chemistry
  • Pargyline / analogs & derivatives
  • Pargyline / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Furans
  • gregatin B
  • gregatin E
  • Palladium
  • Pargyline