Efficient synthesis of the C(1)-C(9) fragment of amphidinolides C, C2, and F

Org Lett. 2010 Nov 5;12(21):4976-9. doi: 10.1021/ol1021228.

Abstract

The synthesis of the C(1)-C(9) fragment of amphidinolides C, C2, and F was achieved by using a vinyloguous Mukaiyama aldol reaction on a chiral aldehyde with a silyloxyfuran and by using a C-glycosylation of a lactol derivative with an acetyl oxazolidinethione. From the available chiral acetonide-glyceraldehyde, all the stereogenic centers were perfectly induced along the synthesis. The C(1)-C(9) fragment was synthesized as a vinyl stannane at C(9) in 10 steps, with 16% yield.

MeSH terms

  • Carbon / chemistry*
  • Macrolides / chemical synthesis*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Macrolides
  • amphidinolide C
  • amphidinolide C2
  • amphidinolide F
  • Carbon