A concise enantioselective synthesis of antimalarial febrifugine alkaloids

Hidenori Ooi, Ayumi Urushibara, Tomoyuki Esumi, Yoshiharu Iwabuchi, Susumi Hatakeyama

Research output: Contribution to journalArticlepeer-review

81 Citations (Scopus)

Abstract

matrix presented Reaction of (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal with hydroxylamine in allyl alcohol brought about simultaneous 1,3-dipolar cycloaddition of the resulting nitrone to allyl alcohol to give three diastereoisomeric adducts, from which (+)-febrifugine and (+)-isofebrifugine, potent antimalarial alkaloids, were synthesized.

Original languageEnglish
Pages (from-to)953-955
Number of pages3
JournalOrganic letters
Volume3
Issue number6
DOIs
Publication statusPublished - 2001 Mar 22
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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