Naturally occurring cytotoxic products, specifically (+)-crassalactone A, from <i>Polyalthia crassa</i> have been of recent synthetic interest. While there have been three total syntheses of (+)-crassalactone A published in recent years by Shekhar et al in 2010, Yadav et al in 2013, and Reddy et al in 2015, a different approach would be to perform an asymmetric hetero Diels-Alder, HDA, reaction that could allow easier access to the styryl lactone core found in (+)-crassalactone A. Building from previous model studies, the approach begins with monoprotection of commercially available (<i>Z</i>)-2-butene-1,4-diol. This is followed by oxidation of the resulting allylic alcohol and formation of a siloxy diene. The approach culminates with testing the siloxy diene under HDA conditions with various dienophiles, such as ethyl glyoxalate. This HDA approach can provide a rapid synthesis and variability of the styryl lactone core present in (+)-crasslactone A for further studies.

Progress towards the synthesis of (+)-crassalactone A via a hetero Diels-Alder approach

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.