Intermolecular radical addition to N-acylhydrazones as a stereocontrol strategy for alkaloid synthesis: formal synthesis of quinine

GK Friestad, A Ji, CS Korapala, J Qin

文献索引：Friestad, Gregory K.; Ji, An; Korapala, Chandra Sekhar; Qin, Jun Organic and Biomolecular Chemistry, 2011 , vol. 9, # 11 p. 4039 - 4043

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被引用次数: 8

摘要

Stereocontrolled Mn-mediated radical addition of alkyl iodides to chiral N-acylhydrazones enables strategic C–C bond disconnection of chiral amines. This strategy was examined in the context of a total synthesis of quinine, generating new findings of functional group compatibility leading to a revised strategy. Completion of a formal synthesis of quinine is presented, validating the application of Mn-mediated radical addition as a useful new C–C ...