Synthesis of EFdA via a diastereoselective aldol reaction of a protected 3-keto furanose

Kei Fukuyama, Hiroshi Ohrui, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

An efficient enantioselective total synthesis of EFdA, a remarkably potent anti-HIV nucleoside analogue with various favorable pharmacological profiles, has been achieved in 37% overall yield from diacetone-d-glucose by a 14-step sequence that features a highly diastereoselective installation of the tetrasubstituted stereogenic center at the C4′ position, direct oxidative cleavage of an acetonide-protected diol derivative to an aldehyde, and one-pot 2′-deoxygenation of a ribonucleoside intermediate.

Original languageEnglish
Pages (from-to)828-831
Number of pages4
JournalOrganic letters
Volume17
Issue number4
DOIs
Publication statusPublished - 2015 Feb 20

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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