Title of article :
First total synthesis and determination of the absolute configuration of 1-N-methyl-3-methylamino-[N-butanoicacid-3-(9-methyl-8-propen-7-one)-amide]-benzo[f][1,7]naphthyridine-2-one, a novel benzonaphthyridine alkaloid
Author/Authors :
Tian، نويسنده , , Chengsen and Jiao، نويسنده , , Xiaozhen and Liu، نويسنده , , Xiaoyu and Li، نويسنده , , Renze and Dong، نويسنده , , Liang and Liu، نويسنده , , Xiaojin and Zhang، نويسنده , , Zhigang and Xu، نويسنده , , Jun and Xu، نويسنده , , Minjuan and Xie، نويسنده , , Ping، نويسنده ,
Abstract :
The first total synthesis of benzonaphthyridine alkaloid (1), a unique diazaphenathrene alkaloid isolated from mangrove-derived Streptomyces albogriseolus, was accomplished. The core structure was unequivocally constructed via several key transformations, such as Knoevenagel condensation, Curtius rearrangement, and cyclic carbamate formation–reduction sequence. The chiral unsaturated ketone acid moiety was synthesized from N-tert-butoxycarbonyl-l-glutamic acid gamma-tert-butyl ester (15). The absolute configuration was determined.
Keywords :
natural product , total synthesis , Benzonaphthyridine alkaloid , absolute configuration
