An iterative Suzuki-Miyaura approach for preparing a conjugated (<i>E,Z,Z,E</i>) tetraene using boronic acids and MIDA-protected boronates will be described. The tetraene undergoes tandem 8π-6π electrocyclizations to yield two diastereomeric bicycles. These diastereomers converge on a single product in a subsequent intramolecular Diels-Alder reaction, generating the tetracyclic core of cryptobeilic acid D and related natural products. Computational results for biosynthetically-relevant intramolecular Diels-Alder reactions with competing regiochemical outcomes (for fused or bridged tetracycles) will also be presented. These combined synthetic and theoretical studies are being applied to endiandric-type plant metabolites with anti-inflammatory, antitubercular, antimalarial, and antibiotic properties.

Iterative Suzuki couplings and biomimetic Diels-Alder reactions to fused and bridged tetracycles: Synthetic and computational results

251st National Meeting (2016)

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