2808-41-5Relevant articles and documents
Syntheses of Amorfrutins and Derivatives via Tandem Diels-Alder and Anionic Cascade Approaches
Curtis, Brian J.,Micikas, Robert J.,Burkhardt, Russell N.,Smith, Rubin A.,Pan, Judy Y.,Jander, Katrina,Schroeder, Frank C.
, p. 11269 - 11276 (2021)
We describe two complementary approaches based on a convergent [4+2] logic toward the synthesis of amorfrutins, cannabinoids, and related plant metabolites. An anionic cascade cyclization employing β-methoxycrotonates and β-chloro-α,β-unsaturated esters yielded amorfrutins in four linear steps and demonstrated utility of β-alkoxycrotonate-derived nucleophiles as functional equivalents of β-ketoester-derived dianions. Analogously, tandem Diels-Alder/retro-Diels-Alder cycloaddition of dimedone-derived bis(trimethylsiloxy)-dienes and α,β-alkynyl ester dienophiles provided facile access to resorcinol precursors of amorfrutins and cannabinoids, avoiding late-stage installation of prenyl or geranyl moieties as in previous approaches.
