Harvey, Ross S.; Mackay, Emily G.; Roger, Lukas; Paddon-Row, Michael N.; Sherburn, Michael S.; Lawrence, Andrew L.
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.
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