An efficient, PIFA mediated approach to benzo-, naphtho-, and heterocycle-fused pyrrolo[2,1-c][1,4]diazepines.: An advantageous access to the antitumor antibiotic DC-81

被引:77
作者
Correa, A [1 ]
Tellitu, I [1 ]
Domínguez, E [1 ]
Moreno, I [1 ]
SanMartin, R [1 ]
机构
[1] Univ Basque Country, Dept Quim Organ 2, Fac Ciencia & Tecnol, EHU, E-48080 Bilbao, Spain
关键词
D O I
10.1021/jo047872u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a series of optically pure benzo-, naphtho-, and heterocycle-fused pyrrolo[2,1-c]-[1,4]-diazepin-5,11-dione derivatives starting from L-proline methyl ester is presented. The synthetic plan includes an aroylation step at the proline nitrogen followed by transformation of the ester residue into a N-methoxyamide group. The subsequent key cyclization step embraces the PIFA mediated formation of a N-acylnitrenium intermediate and its succeeding intramolecular trapping by the aromatic ring. The presented general approach solves the need of starting from not very accessible amino (or a related functionality) aromatic starting materials, and its effectiveness is demonstrated in the synthesis of the antitumor antibiotic DC-81.
引用
收藏
页码:2256 / 2264
页数:9
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