Organosilanes in synthesis: application to an enantioselective synthesis of methyl-l-callipeltose.
[reaction: see text] Methyl-l-callipeltose, the carbohydrate associated with callipeltoside A, has been synthesized in eight steps and 23% overall yield from enantioenriched allylsilane 6 and acetaldehyde. The key steps are a highly diastereoselective formal [4 + 2] annulation and a Cr(VI)-catalyzed oxidative C-C bond cleavage to produce lactone 11.
Huang
Hongbing
H
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Panek
James S
JS
D000606:Amino Sugars / Q000138:chemical synthesis*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002384:Catalysis; D002857:Chromium; D007202:Indicators and Reagents; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D011161:Porifera / Q000737:chemistry; D012821:Silanes; D013237:Stereoisomerism
D000606:Amino Sugars; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D018942:Macrolides; D012821:Silanes; C410329:callipeltoside A; C476920:methyl-L-callipeltose; D002857:Chromium