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Intermolecular Diels-Alder Cycloaddition for the Construction of Bicyclo[2.2.2]diazaoctane Structures: Formal Synthesis of Brevianamide B and Premalbrancheamide
Robins, Jacob G. Kim, Kyu J. Chinn, Alex J. Woo, John S. Scheerer, Jonathan R.
Robins, Jacob G.
Kim, Kyu J.
Chinn, Alex J.
Woo, John S.
Scheerer, Jonathan R.
Abstract
A stereoselective intermolecular Diels-Alder cycloaddition of an intermediate pyrazinone with both achiral and chiral acrylate-derived dienophiles provides rapid access to the bicyclo[2.2.2]diazaoctane core shared among several prenylated indole alkaloids. The product derived from cydoaddition with 2-nitroacrylate required an additional five to six synthetic operations to intercept established precursors to premalbrancheamide and brevianamide B. The chemistry detailed in this manuscript constitutes a formal total synthesis (12 steps each) of these [2.2.2]diazabicyclic natural products from proline methyl ester.
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2016-01-01
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Chemistry
DOI
10.1021/acs.joc.5b02744