An aldol-based approach to the synthesis of the antibiotic anisomycin.
[reaction: see text] A new approach to the synthesis of the antibiotic anisomycin is reported that relies upon a key aldol disconnection. The glycolate aldol coupling proceeds in 75% yield and with >95% diastereoselectivity, which allows the 13-step synthesis to proceed in 35% overall yield.
Hulme
Alison N
AN
Department of Chemistry, The University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, UK.
Rosser
Edward M
EM
D000447:Aldehydes / Q000737:chemistry; D000841:Anisomycin / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D006016:Glycolates / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D006016:Glycolates; C031149:glycolic acid; D000841:Anisomycin; C116609:3-hydroxybutanal