TOWARDS TERPENOID SCAFFOLDS VIA MULTI-FUNCTIONALIZATION OF KNOEVENAGEL ADDUCTS

Peter Vertesaljai, Matthew Williams, and Alexander J. Grenning

Department of Chemistry, University of Florida, Gainesville FL 32611-7200, USA

Knoevenagel adducts obtained from inexpensive ketones and malonic acid derivatives readily undergo selective transformations under mild conditions which makes them attractive building blocks. Our research focuses on the utility of Knoevenagel adducts in scalable, divergent syntheses towards terpenoid natural products and their analogs. A sequence of alkylation/[3,3]-sigmatropic rearrangement/α-alkylation/ring-closing metathesis was devised to construct a library of angular polycyclic carbon frameworks. Diversity is introduced by proper choice of starting materials as well as late stage functional group interconversion.
Another study based on selective functionalization allowed for the synthesis of highly substituted perhydroindoles. Experiments were aimed at outlining the scope and understanding the reactivity of such structures.