Stereoselective synthesis of d-desosamine and related glycals via tungsten-catalyzed alkynol cycloisomerization

Org Lett. 2004 May 13;6(10):1601-3. doi: 10.1021/ol049630m.

Abstract

Stereoselective synthesis of d-desosamine diacetate ester (iii, R = Ac) was achieved from the glycal (ii). generated by tungsten carbonyl-catalyzed cycloisomerization of the corresponding amino-alkynol (i). A wide variety of N-substituents (R, R') are compatible with the cycloisomerization, provided that at least one R or R' is an acyl derivative.

Publication types

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

MeSH terms

  • Alcohols / chemistry*
  • Amino Sugars / chemical synthesis*
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Stereoisomerism
  • Tungsten / chemistry*

Substances

  • Alcohols
  • Amino Sugars
  • desosamine
  • Tungsten