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Asymmetric Total Syntheses of (-)-Angustureine and (-)-Cuspareine via Rhodium-Catalyzed Hydroamination.

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Concise syntheses of the Hancock alkaloids (-)-angustureine and (-)-cuspareine are presented, applying and refining a recently developed rhodium-catalyzed hydroamination for the stereoselective construction of the chiral secondary amine. Furthermore, the… Click to show full abstract

Concise syntheses of the Hancock alkaloids (-)-angustureine and (-)-cuspareine are presented, applying and refining a recently developed rhodium-catalyzed hydroamination for the stereoselective construction of the chiral secondary amine. Furthermore, the syntheses include an allene synthesis via boron-magnesium exchange as well as the construction of the tetrahydroquinoline motive via a hydroboration/Suzuki-Miyaura coupling sequence.

Keywords: rhodium catalyzed; catalyzed hydroamination; angustureine cuspareine

Journal Title: Organic letters
Year Published: 2019

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