1.
J Org Chem
; 86(16): 11269-11276, 2021 08 20.
Artículo
en Inglés
| MEDLINE
| ID: mdl-33661630
RESUMEN
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 ß-methoxycrotonates and ß-chloro-α,ß-unsaturated esters yielded amorfrutins in four linear steps and demonstrated utility of ß-alkoxycrotonate-derived nucleophiles as functional equivalents of ß-ketoester-derived dianions. Analogously, tandem Diels-Alder/retro-Diels-Alder cycloaddition of dimedone-derived bis(trimethylsiloxy)-dienes and α,ß-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.