Total Synthesis and Cytotoxic Activity of 6,8-Dimethoxy-1,3-dimethylisoquinoline Isolated from Ancistrocladus tectorius : A 6-Azaelectrocyclization Approach

被引：8
作者：
Cortes, Ivan [1 ,2 ]
Borini Etichetti, Carla M. [2 ,3 ]
Girardini, Javier E. [2 ,3 ]
Kaufman, Teodoro S. [1 ,2 ]
Bracca, Andrea B. J. [1 ,2 ]
机构：
[1] CONICET UNR, IQUIR, Inst Quim Rosario, Suipacha 531, RA-2000 Rosario, Santa Fe, Argentina
[2] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, Suipacha 531, RA-2000 Rosario, Santa Fe, Argentina
[3] CONICET UNR, Inst Biol Mol & Celular Rosario IBR, RA-2000 Rosario, Argentina
来源：
SYNTHESIS-STUTTGART | 2019年 / 51卷 / 02期
关键词：
total synthesis; bioactive natural product; Ancistrocladus tectorius; alkaloid; 6-azaelectrocyclization; cytotoxic nitrogen heterocycles; NAPHTHYL-ISOQUINOLINE ALKALOIDS; 1ST TOTAL-SYNTHESIS; NAPHTHYLISOQUINOLINE ALKALOIDS; ARYL; INTERMEDIATE; ANCISHEYNINE; TMC-120B; ANALOGS; HALIDES; POTENT;
D O I：
10.1055/s-0037-1610276
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile and convenient approach toward the total synthesis of 1,3-dimethyl-6,8-dimethoxyisoquinoline from phloroacetophenone is reported. The sequence entailed the selective 2,4-di- O -methylation and further triflation of the resulting phenolic product. This was followed by a Stille-type allylation, an allyl-to-propenyl isomerization, and the methoximation of the carbonyl moiety. A final microwave-assisted 6-azaelectrocyclization completed the sequence. Functionalized derivatives on C-1 were also prepared. The heterocycles exhibited cytotoxic activity.
引用
收藏
页码：433 / 440
页数：8
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