Stereodivergent Access to Polyhydroxylated 10-Azabicyclo[4.3.1]decanes as New Calystegine Analogues

Institut de Chimie Organique et Analytique, Université d'Orléans-CNRS UMR 6005, France.
The Journal of Organic Chemistry (Impact Factor: 4.64). 05/2009; 74(8):3179-82. DOI: 10.1021/jo900235d
Source: PubMed

ABSTRACT A rapid and stereodivergent access to polyhydroxylated 10-azabicyclo[4.3.1]decanes as new calystegine analogues by way of a double benzotriazolyl/carbon nucleophile exchange followed by a ring-closing metathesis was achieved. Preliminary evaluation of the new compounds as glucocerebrosidase inhibitors was also performed.

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