Regioselectivity of rhodium nitrene insertion. Syntheses of protected glycals of l-daunosamine, d-saccharosamine, and l-ristosamine |
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Authors: | Parker Kathlyn A Chang Wonsuk |
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Institution: | Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA. kparker@notes.cc sunysb.edu |
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Abstract: | reaction: see text] The carbamate-protected glycals of naturally occurring 3,4-cis-3-amino-2,3,6-trideoxyhexoses (l-daunosamine, d-saccharosamine, and l-ristosamine) were prepared from noncarbohydrate starting materials. The short, high-yield syntheses are based on the chemoselective insertion of a rhodium nitrene in an allylic C-H bond rather than in a C-H bond that is alpha to an oxygen substituent. |
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