An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Readily Available Starting Materials

Angewandte Chemie
Sarah K Scott, Alexander J Grenning

Abstract

Cyclohexanone-derived Knoevenagel adducts (cyclohexylidenemalononitriles) and two different propargyl electrophiles serve as carbon sources for assembling diverse 6/7/5 tricycloalkanes, a common terpenoid framework. The sequence involves three unique reactions: 1) deconjugative propargylation, 2) one-pot enyne Cope rearrangement/deconjugative propargylation, and 3) an allenic Pauson-Khand reaction.

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Citations

Jan 22, 2021·The Journal of Organic Chemistry·Ehsan FereyduniAlexander J Grenning
Jul 17, 2021·Journal of the American Chemical Society·Kohsuke OhmatsuTakashi Ooi
Jan 9, 2018·Journal of the American Chemical Society·Emily E Robinson, Regan J Thomson
Nov 1, 2018·Journal of the American Chemical Society·Sarah K ScottAlexander J Grenning
Mar 23, 2018·Organic Letters·Peter VertesaljaiAlexander J Grenning
Jul 3, 2019·Organic Letters·Peter VertesaljaiAlexander J Grenning

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