A concise route to the highly-functionalized azetidine precursor: the enantioselective synthesis of penaresidin B

Chem Commun (Camb). 2015 Mar 18;51(22):4639-42. doi: 10.1039/c4cc09904d.

Abstract

An efficient and high-yielding synthesis of penaresidin B is disclosed herein. The concise 8-step synthesis of azetidine aldehyde was devised by incorporating our novel strategy for ready access to 3-amino-2,3-dideoxysugars via regio- and stereoselective tandem hydroamination/glycosylation of glycal as the key step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis
  • Aldehydes / chemistry*
  • Azetidines / chemical synthesis*
  • Azetidines / chemistry*
  • Fatty Alcohols / chemical synthesis*
  • Fatty Alcohols / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Aldehydes
  • Azetidines
  • Fatty Alcohols
  • penaresidin B
  • azetidine