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J Am Chem Soc. 2010 Jun 2;132(21):7540-8. doi: 10.1021/ja102623j.

Total synthesis and biological evaluation of the resveratrol-derived polyphenol natural products hopeanol and hopeahainol A.

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  • 1Chemical Synthesis Laboratory at Biopolis, Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, 11 Biopolis Way, The Helios Block, 03-08, Singapore 138667. kcn@scripps.edu

Abstract

The total synthesis and biological evaluation of the resveratrol-derived natural products hopeanol (2) and hopeahainol A (3) in their racemic and antipodal forms are described. The Friedel-Crafts-based synthetic strategy employed was developed from model studies that established the feasibility of constructing the C(7b) quaternary center through an intramolecular Friedel-Crafts reaction and a Grob-type fragmentation to introduce an obligatory olefinic bond in the growing molecule. The final stages of the synthesis involved an epoxide substrate and an intramolecular Friedel-Crafts reaction, followed by oxidation to afford, upon global deprotection, hopeahainol A (3). The latter was converted under basic conditions to hopeanol (2), whereas the reverse transformation, previously suggested as a step in the biosynthesis of hopeahainol A (3), was not observed under a variety of conditions. Biological evaluation of the synthesized compounds confirmed the reported acetylcholinesterase inhibitory activity of hopeahainol A (3) but not the reported cytotoxic potencies of hopeanol (2).

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