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Diastereoselective synthesis of a spironoraristeromycin using an acylnitroso Diels-Alder reaction.

ABSTRACT: The tert-butyl N-hydroxycarbamate-derived nitroso reagent 1 reacted with N-Cbz-protected spirocyclic diene 2 to provide spirocycloadduct 3. Here we describe the efficient conversion of 3 into the novel carbocyclic nucleoside spironoraristeromycin 4.

SUBMITTER: Lin W 

PROVIDER: S-EPMC2888906 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Diastereoselective synthesis of a spironoraristeromycin using an acylnitroso Diels-Alder reaction.

Lin Weimin W   Virga Kristopher G KG   Kim Kyung-Hee KH   Zajicek Jaroslav J   Mendel David D   Miller Marvin J MJ  

The Journal of organic chemistry 20090801 16

The tert-butyl N-hydroxycarbamate-derived nitroso reagent 1 reacted with N-Cbz-protected spirocyclic diene 2 to provide spirocycloadduct 3. Here we describe the efficient conversion of 3 into the novel carbocyclic nucleoside spironoraristeromycin 4. ...[more]

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