Synthetic studies on (+)-naphthyridinomycin: stereoselective synthesis of the tetracyclic core framework.
[reaction: see text] The stereoselective synthesis of the tetracyclic intermediate 21 for (+)-naphthyridinomycin (1) has been accomplished. The convergent synthesis used the Ugi 4CC reaction with the amine derivative 10. The key features of the stereoselective synthesis of 21 were the intramolecular Mizoroki-Heck reaction, an aromatic-aldehyde cyclization, and a stereoselective hydroboration.
Mori
Kazuki
K
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, Japan.
Rikimaru
Kentaro
K
Kan
Toshiyuki
T
Fukuyama
Tohru
T
D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis; D013237:Stereoisomerism
D007202:Indicators and Reagents; D009287:Naphthyridines; C010752:naphthyridinomycin