SPIRO-ACTIVATED CYCLOPROPANES: VERSATILE INTERMEDIATES FOR THE TOTAL SYNTHESIS OF NATURAL PRODUCTS
LIVINGHOUSE, THOMAS STUART
Doctor of Philosophy
A novel approach to natural product synthesis is presented herein which encompasses three original functionalization processes. These are; (a) the direct photochemical conversion of alkenes to spiro-activated cyclopropanes, (b) the homoconjugate addition of organo-magnesium reagents to said cyclopropanes, and (c) the ozonolysis of isopropylidene malonate enolates. An application of this new methodology to the partial synthesis of racemic brefeldin A is then described.