Cationic reduction of bastadin-4 to bastadin-5. Preparation of 5-[2h]-bastadin-5 by site-specific isotopic labeling

J Nat Prod. 2003 Jan;66(1):112-4. doi: 10.1021/np020382h.

Abstract

A chemoselective conversion of bastadin-4 to the important Ca2+ channel modulator bastadin-5 (1a) has been achieved using cationic hydrogenation (Et3SiH, TFA, 60%). Specifically deuterated bastadin-5 (1b, >95 at. %) was prepared following this method and the simplified 1H NMR H-5/H2-6 spin system of 1b exploited to study temperature-dependent macrocyclic ring dynamics.

Publication types

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

MeSH terms

  • Animals
  • Calcium Channel Agonists / chemical synthesis*
  • Calcium Channel Agonists / pharmacology
  • Cyclization
  • Halogenated Diphenyl Ethers
  • Hydrogenation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxidation-Reduction
  • Phenyl Ethers / chemical synthesis*
  • Phenyl Ethers / chemistry*
  • Phenyl Ethers / pharmacology
  • Porifera / chemistry*
  • Temperature

Substances

  • Calcium Channel Agonists
  • Halogenated Diphenyl Ethers
  • Phenyl Ethers
  • bastadin 4
  • bastadin 5