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 ,
Issue Information
هفته نامه با شماره پیاپی سال 2012
Pages
4
From page
4892
To page
4895
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
Journal title
Tetrahedron Letters
Serial Year
2012
Journal title
Tetrahedron Letters
Record number
1881741
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