Total synthesis of ramonanins A-D.
The first total synthesis of the ramonanin family of lignan natural products is described. The short synthesis involves a 2,5-diaryl-3,4-dimethylene tetrahydrofuran intermediate, which participates in an unexpectedly facile Diels-Alder dimerization, generating all four natural products. Insights into the reactivity and stereoselectivity of the key dimerization are provided through computational studies employing B3LYP/6-31G(d) and M06-2X/6-31G(d) model chemistries.
['Harvey|Ross S|RS|', 'Mackay|Emily G|EG|', 'Roger|Lukas|L|', 'Paddon-Row|Michael N|MN|', 'Sherburn|Michael S|MS|', 'Lawrence|Andrew L|AL|']
D001688:Biological Products D017705:Lignans
lignans natural products Diels-Alder reactions biomimetic synthesis enyne metathesis