Formal synthesis of (+/-)-platensimycin

Org Lett. 2007 Apr 26;9(9):1825-8. doi: 10.1021/ol070563g. Epub 2007 Apr 4.

Abstract

[reaction: see text] Reductive alkylation of 5-methoxy-1-tetralone (6) with 2,3-dibromopropene gave an equilibrium mixture of bicyclic diones 7 (51%) and 8 (35%). Radical cyclization of 7 afforded tricyclic dione 5 (84%), which was reduced, cyclized, and dehydrated to give tetracyclic alkene 13 in 63% yield. Allylic oxidation of 13 with SeO2 and activated MnO2 afforded enone 2 in 85% yield, thereby completing a short formal synthesis of (+/-)-platensimycin.

Publication types

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

MeSH terms

  • Adamantane / chemical synthesis*
  • Adamantane / chemistry
  • Aminobenzoates / chemical synthesis*
  • Aminobenzoates / chemistry
  • Anilides / chemical synthesis*
  • Anilides / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Molecular Structure
  • Oxidation-Reduction
  • Water / chemistry

Substances

  • Aminobenzoates
  • Anilides
  • Water
  • Adamantane
  • platensimycin