April 15, 2008

Anodic Cyclization Reactions and the Synthesis of (−)-Crobarbatic Acid

Hai-Chao Xua, John D. Brandta and Kevin D. Moeller
Tetrahedron Letters, 2008, 49(24), 3868-3871

A synthesis of (−)-crobarbatic acid is reported along with the first use of a vinyl-substituted ketene dithioacetal as a coupling partner for an anodic cyclization reaction. The use of the vinyl-substituted ketene dithioacetal enables the construction of a cyclic product having a tetrasubstituted carbon with a relative stereochemistry opposite to that originally obtained from the cyclization.