Catalytic asymmetric synthesis of CPZEN-45. Issue 26 (29th June 2016)

• Record Type: Journal Article
• Authors: Takeuchi, Toshifumi; Abe, Hikaru; Watanabe, Takumi; Shibasaki, Masakatsu
• Is Part Of: Tetrahedron letters. Volume 57:Issue 26(2016)
• Page Start: 2901
• Page End: 2904
• Publication Date: 2016-06-29
• Subjects: CPZEN-45 -- Catalytic asymmetric aldol reaction -- Anti-XDR-TB agent; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.072
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Catalytic asymmetric total synthesis of CPZEN-45 was achieved. A direct aldol reaction catalyzed by Zn(II)–( R, R )-linked-BINOL complex furnished a key stereochemical element. The diazepinone ring system was constructed by Cu-mediated vinyl halide–amide coupling. Abstract: A catalytic asymmetric total synthesis of CPZEN-45 (1 ), anti-XDR-TB agent, was accomplished using a direct aldol reaction of a glycine Schiff base (3 ) and uridine-derived aldehyde (4 ) catalyzed by Zn(II)–( R, R )-linked-BINOL complex to give the desired stereoisomer selectively. The diazepinone ring system, another key structural element, was successfully constructed by vinyl halide–amide coupling promoted by Cu(I) salt.