Literature DB >> 11263924

A concise enantioselective synthesis of antimalarial febrifugine alkaloids.

H Ooi1, A Urushibara, T Esumi, Y Iwabuchi, S Hatakeyama.   

Abstract

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.

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Year:  2001        PMID: 11263924     DOI: 10.1021/ol015655z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  A chiral Lewis acid strategy for enantioselective allylic C-H oxidation.

Authors:  Dustin J Covell; M Christina White
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 2.  The role of biocatalysis in the asymmetric synthesis of alkaloids.

Authors:  Joerg H Schrittwieser; Verena Resch
Journal:  RSC Adv       Date:  2013-08-07       Impact factor: 3.361

  2 in total

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