Synthetic Approach to the Elisapterosins and Cumbiasins

University Of California Irvine, Irvine CA

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Abstract

The elisapterosins, cumbiasins and colombiasin A are an unusual and novel class of Gorgonian octocorals isolated from Psuedopterogorgia. Initial biological tests have found these metabolites to display mild to strong in vitro antituberculosis activity. However, as with many marine natural products, the amount of material available from natural sources is scarce thus making broad spectrum biological screening and advanced testing impossible. Therefore, total synthesis is the only means by which substantial quantities of material can be obtained. An original approach to the synthesis of the elisapterosins, cumbiasins and colombiasin A will be described herein. Key features presented in the approach include rapid construction of a decalin intermediate by an asymmetric phenolic oxidation trapping sequence that is followed by a domino Diels- Alder/Cope rearrangement. Finally, a Prins-pinacol rearrangement provides access to the angular cyclopentane ring system found in this class of natural products. The densely functionalized complex nature of these natural products creates a formidable challenge for synthesis; however, the proposed strategy allows for a concise (21 steps, best case) enantioselective synthesis of this class of molecules.