SmI2-Mediated Radical Coupling Strategy to Securinega Alkaloids: Total Synthesis of (−)-14,15-Dihydrosecurinine and Formal Total Synthesis of (−)-Securinine

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The asymmetric total synthesis of (-)-14,15-dihydrosecurinine and the formal total synthesis of (-)-securinine were accomplished starting from an easily available malimide. A concise SmI2-mediated radical coupling strategy has been developed to construct the bridged α-hydroxy 6-azabicyclo[3.2.1]octanone in four steps with high diastereoselectivity.