Science and Technology Production
Total synthesis and cytotoxic activity of 6,8‐dimethoxy‐1,3‐ dimethylisoquinoline, isolated from Ancistrocladus tectorius. A 6π‐ azaelectrocyclization approach
Article
Authorship:
CORTÉS, IVÁN ; Carla M. Borini Etichetti ; Javier E. Girardini ; Teodoro S. Kaufman ; Andrea B.J. BraccaDate:
2018Publishing House and Editing Place:
GEORG THIEME VERLAG KGMagazine:
SYNTHESIS-STUTTGART GEORG THIEME VERLAG KGSummary *
A facile and convenient approach toward the total synthesis of 1,3‐ dimethyl‐6,8‐dimethoxy isoquinoline 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 microwaves‐assisted 6π‐azaelectrocylization completed the sequence. Functionalized derivatives on C‐1 were also prepared. The heterocycles exhibited cytotoxic activity. Information provided by the agent in SIGEVAKey Words
ANCISTROCLADUS TECTORIUS ALKALOIDBIOACTIVE NATURAL PRODUCTTOTAL SYNTHESIS6π‐AZAELECTROCYCLIZATION