Total synthesis of both methyl 4a-carba-D-arabinofuranosides.
[reaction: see text] The total synthesis of methyl 4a-carba-alpha-D-arabinofuranoside (1) and methyl 4a-carba-beta-D-arabinofuranoside (2) has been achieved starting from D-mannose (5). Key transformations included a ring-closing metathesis of diene 11 employing Schrock's catalyst followed by a stereoselective hydrogenation with Wilkinson's catalyst.
Callam
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Department of Chemistry, The Ohio State University, Columbus 43210, USA.
Lowary
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D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D000995:Antitubercular Agents / Q000138:chemical synthesis; D002473:Cell Wall / Q000737:chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D008958:Models, Molecular; D009169:Mycobacterium tuberculosis / Q000648:ultrastructure; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D000995:Antitubercular Agents; D003517:Cyclopentanes; D006027:Glycosides