Enantioselective Total Synthesis of (+)-Amphirionin-4

Org Lett. 2016 May 6;18(9):2296-9. doi: 10.1021/acs.orglett.6b00942. Epub 2016 Apr 26.

Abstract

An enantioselective total synthesis of (+)-amphirionin-4 has been accomplished in a convergent manner. The synthesis features an efficient enzymatic lipase resolution to access the tetrahydrofuranol core in optically active form. The functionalized tetrahydrofuran derivative was synthesized via an oxocarbenium ion-mediated highly diastereoselective syn-allylation reaction. The polyene side chain was synthesized using Stille coupling reactions. Nozaki-Hiyama-Kishi coupling was utilized to construct the C-8 stereocenter and complete the synthesis of (+)-amphirionin-4.

Publication types

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

MeSH terms

  • Molecular Conformation
  • Polyketides / chemical synthesis*
  • Polyketides / chemistry
  • Stereoisomerism

Substances

  • Polyketides
  • amphirionin-4