A new simple route to deoxyamino sugars from non-sugar material: synthesis of d-tolyposamine and 4-epi-d-tolyposamine and formal synthesis of d-vicenisamine |
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Authors: | Yoshitaka Matsushima Jun Kino |
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Affiliation: | Department of Chemistry, Hamamatsu University School of Medicine, Handayama, Hamamatsu 431-3192, Japan |
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Abstract: | A new, simple strategy has been formulated for the synthesis of deoxyamino sugars from a non-sugar starting material. Starting from the enantiomerically pure diol obtained from ethyl sorbate by Sharpless asymmetric dihydroxylation, the synthesis of two types of 2,3,4,6-tetradeoxy-4-amino sugars—d-tolyposamine and 4-epi-d-tolyposamine—, and formal synthesis of 2,4,6-trideoxy-4-amino sugar—d-vicenisamine—were performed. |
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Keywords: | Deoxyamino sugar Sharpless asymmetric dihydroxylation Tolyposamine Iodocyclisation Vicenisamine |
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