Sotiris Petrides

A study toward synthesis of the natural product Ansellone A and other terpenoid compounds from the same family is under way in our laboratory. These are recently discovered sesterpenoid natural products with interesting biological activities, such as cAMP pathway activation and HIV latency reversal. Two building blocks from the commercially available chiral terpene pool have been exploited for the production of the two constituent halves of Ansellone A, affording direct access to some of the desired stereocenters. This is expected to minimize the number of synthetic steps required and to control stereochemistry in downstream steps. The involved chemistry toolbox includes regioselective allylic chlorination, umpolung reaction and α-hydroxylation of carbonyl intermediates. Furthermore, metal-mediated conditions for establishing a connection between the two halves are under investigation, while elaboration of an advanced intermediate into the final product is expected to require additional allylic CH functionalization.