A bidirectional approach to the synthesis of a complete library of adjacent-bis-THF annonaceous acetogenins. Academic Article uri icon

Overview

abstract

  • Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved.

publication date

  • July 22, 2005

Research

keywords

  • Annonaceae
  • Antineoplastic Agents, Phytogenic
  • Fatty Alcohols
  • Furans
  • Lactones

Identity

Scopus Document Identifier

  • 22244473283

PubMed ID

  • 16018687

Additional Document Info

volume

  • 70

issue

  • 15