A scalable synthesis of an azabicyclooctanyl derivative, a novel DPP-4 inhibitor

…, S Xue, J McKenna, K Prasad, M Prashad…

文献索引：Fei, Zhongbo; Wu, Quanbing; Zhang, Fei; Cao, Yudong; Liu, Chuanqin; Shieh, Wen-Chung; Xue, Song; McKenna, Joe; Prasad, Kapa; Prashad, Mahavir; Baeschlin, Daniel; Namoto, Kenji Journal of Organic Chemistry, 2008 , vol. 73, # 22 p. 9016 - 9021

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被引用次数: 14

摘要

A practical synthetic strategy to a chiral azabicycclooctanyl derivative (1), a potent DPP-4 inhibitor, starting from a commercially available nortropine is described. The stereogenic center of 1 was established employing a modified protocol of Ellman's diastereoselective addition of a benzylic nucleophile to tert-butanesulfinimine. Other key steps include Corey− Chaykovsky reaction, Meinwald rearrangement, and CDMT-promoted amide bond ...