An aldol-based approach to the asymmetric synthesis of L-callipeltose, the deoxyamino sugar of L-callipeltoside A.
[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.
Evans
D A
DA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Hu
E
E
Tedrow
J S
JS
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
D000606:Amino Sugars; D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D018942:Macrolides; C438929:callipeltose; C410329:callipeltoside A; D013912:Threonine