Studies toward the synthesis of pinnatoxins: the B,C,D-dispiroketal fragment

Org Lett. 2007 Aug 2;9(16):3161-3. doi: 10.1021/ol071266e. Epub 2007 Jul 12.

Abstract

A stereoselective synthesis of the tricyclic B,C,D-dispiroketal fragment of pinnatoxins is described. Both products of an efficient enzymatic resolution reaction are used to set the stereochemistry of C12 and C23, which have opposite configuration. The configuration of the ketal centers is established upon an optimized thermodynamically controlled spiroketalization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry*
  • Stereoisomerism
  • Thermodynamics

Substances

  • Alkaloids
  • Spiro Compounds
  • pinnatoxin B