Anodic cyclization reactions: the total synthesis of alliacol a.
An anodic cyclization-Friedel Crafts alkylation strategy has been used to rapidly assemble the core ring system of alliacol A and to complete a formal total synthesis of the natural product. The anodic cyclization reaction was used to effect the coupling of a nucleophilic furan ring to the normally nucleophilic carbon of a silyl enol ether. The substrate for this initial cyclization reaction contained all of the carbons needed for completing the total synthesis. The electrolysis proceeded in high yield and could be accomplished with the use of a 6 V lantern battery.
Mihelcic
John
J
Department of Chemistry, Washington University, St. Louis, MO 63130, USA.
Moeller
Kevin D
KD
D000838:Anions; D003500:Cyclization; D004563:Electrochemistry / Q000379:methods; D012717:Sesquiterpenes / Q000138:chemical synthesis*
D000838:Anions; D012717:Sesquiterpenes; C032955:alliacol A