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| - A Concise Total Synthesis of the Azaphenanthrene AlkaloidEupolauramine
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| - A six-step total synthesis of the azaphenanthrene alkaloid eupolauramine 1 has been achievedusing combinational metalation−cyclization tactics. The synthetic route involved first the construction of the azaisoindolinone 9 by aryne-mediated cyclization of he phosphorylated pyridocarboxamide7 and subsequent dephosphorylation. Metalation of 9 followed by connection of the hydroxybenzylappendage and E1CB anti-elimination allowed the formation of the halogenoarylmethyleneazaisoindolinone 4 in the exclusive E-form. Oxidative radical cyclization gave rise to theazaphenanthrene skeleton and regioselective bromination of 3 induced the incorporation of thebromine atom at the 6-position of the azaphenanthrene lactam. Ultimate replacement of the bromineatom of 2 by the methoxy functionality by sequential transmetalation, in situ oxidation, andO-methylation of the phenolic derivative 14 completed the synthesis of the target natural producteupolauramine.
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