A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction

Org Lett. 2010 Jul 2;12(13):2954-7. doi: 10.1021/ol100959a.

Abstract

Homoallylation of aldehydes with isoprene and triethylborane catalyzed by Ni(acac)(2) gave hydroxyalkenes in good yield with excellent regio- and stereoselectivity. Cross metathesis of the hydroxyalkenes with methyl acrylate using second-generation Grubbs catalyst and copper(I) iodide afforded alpha,beta-unsaturated esters, which underwent cyclization in the presence of DBU to produce tetrahydrofurans with the correct relative configuration for the C1-C9 fragment of amphidinolides C, C2, and F.

Publication types

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

MeSH terms

  • Aldehydes / chemistry
  • Boranes / chemistry
  • Butadienes / chemistry
  • Catalysis
  • Hemiterpenes / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Structure
  • Nickel / chemistry
  • Organometallic Compounds / chemistry
  • Pentanes / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Boranes
  • Butadienes
  • Hemiterpenes
  • Macrolides
  • Organometallic Compounds
  • Pentanes
  • amphidinolide C
  • isoprene
  • Nickel
  • triethylborane