Enantiopure α-hydroxy-β-lactams via stereoselective glycosylation

Stereospecific glycosylation via the Ferrier rearrangement catalyzed by iodine has been used to obtain both enantiomers of a trans 4-aryl-3-hydroxy-2-azetidinone. Unexpectedly, a rhamnal derivative had to be employed for this reaction since a glucal derivative failed to work. This synthesis compleme...

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Bibliographic Details
Published inTetrahedron letters Vol. 38; no. 29; pp. 5077 - 5080
Main Authors Banik, Bimal K., Manhas, Maghar S., Bose, Ajay K.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.07.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SIDE-CHAIN
TAXOL
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Summary:Stereospecific glycosylation via the Ferrier rearrangement catalyzed by iodine has been used to obtain both enantiomers of a trans 4-aryl-3-hydroxy-2-azetidinone. Unexpectedly, a rhamnal derivative had to be employed for this reaction since a glucal derivative failed to work. This synthesis complements our previously described preparation of the corresponding cis isomers by the same methodology. Thus, convenient access has become available to all four homochiral stereoisomers of α-hydroxy-β-lactams some of which are synthons for Taxol ® and analogs. Both enantiomers of a trans 4-aryl-3-hydroxy-2-azetidinone have been obtained via stereospecific glycosylation with rhamnal diacetate in presence of iodine (catalyst).
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01130-1