Abstract
A practical synthetic strategy to a chiral azabicycclooctanyl derivative (1), a potent DPP-4 inhibitor, starting from a commercially available nortropine is described. The stereogenic center of 1 was established employing a modified protocol of Ellman's diastereoselective addition of a benzylic nucleophile to tert-butanesulfinimine. Other key steps include Corey-Chaykovsky reaction, Meinwald rearrangement, and CDMT-promoted amide bond formation involving a sterically hindered amine 2.
MeSH terms
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Aldehydes / chemistry
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Azabicyclo Compounds / chemical synthesis*
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Azabicyclo Compounds / chemistry
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Azabicyclo Compounds / pharmacology
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Butanes / chemistry
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Dipeptidyl-Peptidase IV Inhibitors / chemical synthesis*
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Dipeptidyl-Peptidase IV Inhibitors / chemistry
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Dipeptidyl-Peptidase IV Inhibitors / pharmacology
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Imines / chemistry
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Stereoisomerism
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Sulfonium Compounds / chemistry
Substances
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Aldehydes
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Azabicyclo Compounds
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Butanes
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Dipeptidyl-Peptidase IV Inhibitors
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Imines
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Sulfonium Compounds
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sulfinimine
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butane