title: An aldol-based approach to the asymmetric synthesis of L-callipeltose, the deoxyamino sugar of L-callipeltoside A.
abstract: [reaction: see text] The L-callipeltose subunit of L-callipeltoside A has been synthesized in 10 steps and 13% overall yield from D-threonine. The key steps are a highly diastereoselective Felkin anti aldol addition to a methyl ketone and a selective methylation of a secondary alcohol in the presence of a secondary carbamate.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
authors.forename: D A
authors.initials: DA
authors.lastname: Evans
authors.forename: E
authors.initials: E
authors.lastname: Hu
authors.forename: J S
authors.initials: JS
authors.lastname: Tedrow
mesh_terms: D000606:Amino Sugars / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis; D018942:Macrolides; D013237:Stereoisomerism; D013912:Threonine / Q000737:chemistry
chemical_list: D000606:Amino Sugars; D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D018942:Macrolides; C438929:callipeltose; C410329:callipeltoside A; D013912:Threonine