Oxidative cyclizations: the asymmetric synthesis of (-)-alliacol A.
A tandem anodic coupling-Friedel-Crafts alkylation strategy has been used to rapidly complete the asymmetric synthesis of alliacol A. The anodic oxidation reaction allowed for the generation of a new bond between two nucleophiles. In the synthesis, the absolute stereochemistry of the final natural product is set relative to a methyl group that is incorporated early in the sequence using an asymmetric Michael reaction.
Mihelcic
John
J
Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
Moeller
Kevin D
KD
D000363:Agaricales / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D012717:Sesquiterpenes; C032955:alliacol A