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

Abstract 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...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2019, Vol.51 (2), p.433-440
Main Authors: Cortés, Iván, Borini Etichetti, Carla M., Girardini, Javier E., Kaufman, Teodoro S., Bracca, Andrea B. J.
Format: Article
Language:English
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Summary:Abstract 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 6π-azaelectrocyclization completed the sequence. Functionalized derivatives on C-1 were also prepared. The heterocycles exhibited cytotoxic activity.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1610276