Total synthesis and stereochemistry of pinnatoxins B and C

Org Lett. 2006 Jul 20;8(15):3327-30. doi: 10.1021/ol0611548.

Abstract

[Structure: see text] Pinnatoxins B and C were synthesized from diols (34R)-3b and (34S)-3a, respectively, in a stereochemically controlled manner. Through extensive analysis of the 1H NMR spectra of synthetic PnTXs B and C, the diagnostic NMR signals were first identified to differentiate (34S)- and (34R)-diastereomers and then used to establish the C34 configuration of natural PnTXs B and C as 34S and 34R, respectively.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Alkaloids
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Shellfish
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Alkaloids
  • Spiro Compounds
  • pinnatoxin B
  • pinnatoxin C