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Keywords:

  • Synthetic methods;
  • Diastereo­selectivity;
  • Lactones;
  • Natural products;
  • Iodolactonization

Abstract

Generalized iodolactonization conditions have been developed for the formation of both cis- and trans-γ-lactones from 3-pentenoic acid derivatives containing various protected alcohol moieties. Kinetic control of the reaction using iodine and base at 0 °C for 6 h provided the cis-lactone with good selectivity (75:25), and thermodynamic control at room temperature for 24 h provided the trans-lactone with excellent selectivity (98:2).