Stereoselective synthesis of the C(1)-C(19) fragment of tetrafibricin

Org Lett. 2007 Feb 1;9(3):533-6. doi: 10.1021/ol0629869.

Abstract

[reaction: see text] A stereoselective synthesis of the C(1)-C(19) fragment of tetrafibricin has been accomplished via a highly diastereoselective double allylboration reaction of 6-8 and an iodonium ion promoted urethane cyclization for the installation of the C(15) alkoxy function in 3.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alcohols / chemistry
  • Allyl Compounds / chemistry
  • Boron / chemistry
  • Cyclization
  • Fibrinolytic Agents / pharmacology*
  • Iodine / chemistry
  • Ions
  • Macrolides / chemical synthesis*
  • Models, Chemical
  • Stereoisomerism
  • Streptomyces / chemistry*
  • Urethane / chemistry

Substances

  • Alcohols
  • Allyl Compounds
  • Fibrinolytic Agents
  • Ions
  • Macrolides
  • alkoxyl radical
  • tetrafibricin
  • Urethane
  • Iodine
  • Boron