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Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso Diels-Alder reactions.

ABSTRACT: N-Cbz- and Boc-protected spirocyclic dienes were prepared by dialkylation of cyclopentadiene. These dienes coupled efficiently in a series of iminonitroso Diels-Alder reactions to produce a series of new spirocyclic adducts. Hydrogenolysis of these adducts afforded new spirocycles that contain multiple handles for further functionalization. Furthermore, stereocontrolled dihydroxylation and reductive cleavage of the spirocyclic adducts generated versatile scaffolds for the syntheses and derivatization of novel spirocyclic carbocyclic nucleoside analogs.

SUBMITTER: Lin W

PROVIDER: S-EPMC2671554 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso Diels-Alder reactions.

Lin Weimin W Gupta Anuradha A Kim Kyung Hee KH Mendel David D Miller Marvin J MJ

Organic letters 20090101 2

N-Cbz- and Boc-protected spirocyclic dienes were prepared by dialkylation of cyclopentadiene. These dienes coupled efficiently in a series of iminonitroso Diels-Alder reactions to produce a series of new spirocyclic adducts. Hydrogenolysis of these adducts afforded new spirocycles that contain multiple handles for further functionalization. Furthermore, stereocontrolled dihydroxylation and reductive cleavage of the spirocyclic adducts generated versatile scaffolds for the syntheses and derivatiz ...[more]

PMID: 19072701

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