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Construction of Bicyclo[2.2.2]diazaoctane Alkaloids via Intermolecular [4+2] Cycloadditions
Robins, Jacob Gabriel
Robins, Jacob Gabriel
Abstract
The synthesis of bicyclo[2.2.2]diazaoctane prenylated indole alkaloids, containing both syn and anti ring fusion, is described. More than 100 examples of alkaloids in this family have been isolated and show a variety of potent bioactivities. This strategy utilizes the convergent and atom–economic intermolecular hetero Diels–Alder cycloaddition to construct the bicyclic nucleus from electron–deficient dienophiles and an electron–rich pyrazinone diene. The regiochemical and stereochemical implications of this cyclization are investigated.
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2016-04-01
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Chemistry