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Construction of Bicyclo[2.2.2]diazaoctane Scaffolds via Intermolecular Diels-Alder: Synthesis of (±)-Brevianamide B and Progress Toward (+)-Serantrypinone
Wang, Xiye
Wang, Xiye
Abstract
This thesis outlines investigations into utilizing an intermolecular Diels-Alder approach to access the bicyclo[2.2.2]diazaoctane motif in natural products. A stereodivergent synthesis of prenylated indole alkaloid scaffolds from a common diene precursor, and a revised synthetic strategy to (±)-brevianamide B was a result of improved understanding of regioselectivity and stereoselectivity of intermolecular [4+2] between pyrazinone-type dienes and fumarate and maleic anhydride type dienophiles. This observed selectivity was also exploited in the synthesis of (+) serantrypinone, as the key Diels-Alder reaction between a chiral-nonracemic diene and an isatin derived dienophile proceeded with endo preference and exclusive regioselectivity. Progress of downstream elaborations from the cycloadduct towards (+)-serantrypinone is also reported.
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2018-12-01
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Chemistry