Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1141-1148
doi:10.1351/pac200880051141
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.
Keywords: chromatographic resolution; computational organometallic chemistry; ketone alkylation; natural product synthesis; spiroketal construction.
*Paper based on a presentation at the 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), 2-6 August 2007, Nara, Japan. Other presentations are published in this issue, pp. 807-1194.