Synthesis of the C3-C18 fragment of amphidinolides G and H

Org Lett. 2007 Aug 2;9(16):3001-4. doi: 10.1021/ol071024e. Epub 2007 Jul 7.

Abstract

A synthesis of an amphidinolides G and H C3-C18 subunits is reported. The C10-C18 segment 4 was prepared by a Negishi cross-coupling, whereas the synthesis of the C3-C9 fragment 5 employed an asymmetric cyanosilylation as the key step. The two segments were coupled by lithiation of iodide 4 and trapping of the anion with amide 5. The allylic epoxide moiety could be synthesized from the protected anti- mesylate 22.

Publication types

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

MeSH terms

  • Catalysis
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Structure

Substances

  • Macrolides
  • amphidinolide G
  • amphidinolide H