Determination of the relative and absolute configuration of the dimethylmyristoyl side chain of pneumocandin B0 by asymmetric synthesis

Org Lett. 2002 Nov 28;4(24):4201-4. doi: 10.1021/ol0261940.

Abstract

[reaction: see text] The relative and absolute configuration of the pneumocandin B(0) side chain has been established as (10R,12S)-dimethylmyristoyl by the stereocontrolled synthesis of both antipodes of the side chain acid and their comparison to a sample derived from the natural product.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry*
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry*
  • Echinocandins
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Peptides*
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry*

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Echinocandins
  • Peptides
  • Peptides, Cyclic
  • pneumocandin B(0)