Document Type
Article
Department/Program
Chemistry
Journal Title
Journal of Organic Chemistry
Pub Date
2016
Volume
81
Issue
6
First Page
2293
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.
Recommended Citation
Robins, Jacob G.; Kim, Kyu J.; Chinn, Alex J.; Woo, John S.; and Scheerer, Jonathan R., Intermolecular Diels-Alder Cycloaddition for the Construction of Bicyclo[2.2.2]diazaoctane Structures: Formal Synthesis of Brevianamide B and Premalbrancheamide (2016). Journal of Organic Chemistry, 81(6), 2293-2301.
10.1021/acs.joc.5b02744
DOI
10.1021/acs.joc.5b02744
