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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1141-1148

Toward the total synthesis of ritterazine N

Douglass F. Taber, Jean-Michel Joerger and Karen V. Taluskie

Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA

Abstract: Zr-mediated equilibrating cyclocarbonylation of a designed triene led with high diastereocontrol to the ABC 6-6-5 tricyclic core of ritterazine N. The 5-5 EF spiroketal side chain of ritterazine N was prepared by equilibrating cyclization of an acyclic keto diol. The two components were coupled, and the D ring was assembled by intramolecular aldol condensation.