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.

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.

中文翻译：

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中华按蚊的6,8-二甲氧基-1,3-二甲基异喹啉的全合成及细胞毒活性：6π-氮杂电环化方法

摘要

报道了一种从邻苯二甲乙酮全合成1，3-二甲基-6，8-二甲氧基异喹啉的简便方法。该序列需要选择性的2，4-二-O-甲基化和进一步的三氟甲基化所得到的酚产物。随后进行Stille型烯丙基化，烯丙基至丙烯基异构化和羰基部分的甲羟肟化。最终的微波辅助6π-氮杂电环化完成了该序列。还制备了C-1上的官能化衍生物。杂环表现出细胞毒性活性。

报道了一种从邻苯二甲乙酮全合成1，3-二甲基-6，8-二甲氧基异喹啉的简便方法。该序列需要选择性的2，4-二-O-甲基化和进一步的三氟甲基化所得到的酚产物。随后进行Stille型烯丙基化，烯丙基至丙烯基异构化和羰基部分的甲羟肟化。最终的微波辅助6π-氮杂电环化完成了该序列。还制备了C-1上的官能化衍生物。杂环表现出细胞毒性活性。