Aromatic nucleophilic substitution or CuI-catalyzed coupling route to martinellic acid

被引:110
作者
Ma, DW [1 ]
Xia, CF [1 ]
Jiang, JQ [1 ]
Zhang, JH [1 ]
Tang, WJ [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/jo026125z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Condensation of beta-amino ester 8b with triflate 7 gives N-aryl amino ester 11, which is converted into 2-substituted 4-oxoquinoline 4 using an intramolecular Dieckmann reaction as the key step. CuI-mediated coupling of beta-amino ester 8a with 1,4-diiodobenzene followed by an intramolecular acylation and Pd-catalyzed carbonylation provide another manner to 4. Alkylation of 4 and subsequent reductive amination deliver the cyclic imine 14, which is transformed into triamine 3 by ordinary operations. Guanylation of 3 under mild condition followed by deprotection results in the synthesis of martinellic acid 1.
引用
收藏
页码:442 / 451
页数:10
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