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我们选择2,4,6-三经基5-羰基-5,12-二氢并四苯(Ⅻ)作为合成脱二甲氨地霉红(Ⅰ)的模型。按照两条可能的合成路线,一条是Ⅱ与Ⅲ在硼酸作用下的缩合,另一条是Ⅴ与Ⅵ的Friedel-Crafts酰化反应,获得同一缩合产物Ⅳ。在Friedel-Crafts反应中除Ⅳ以外还同时得到了Ⅳ的乙酯(Ⅶ)及环化产物(Ⅷ)。将Ⅳ用浓硫酸环化再继之以氢碘酸的作用,得到Ⅻ。Ⅻ也可自Ⅳ进行环化,接著脱甲基化,还原及最后脱甲基化反应制得。曾讨论Ⅻ的结构,并从红外光谱得到证明。
We chose 2,4,6-tricarbyl 5-carbonyl-5,12-dihydrotetracene (tris) as a model for the synthesis of dimethodeimthromycin red (I). According to two possible synthetic routes, one is the condensation of Ⅱ and Ⅲ under boric acid and the other is the Friedel-Crafts acylation of Ⅴ and Ⅵ to obtain the same condensation product Ⅳ. In the Friedel-Crafts reaction, besides IV, the ethyl ester (VII) of IV and the cyclized product (VIII) were also obtained. The Ⅳ with concentrated sulfuric acid cyclization followed by the role of hydroiodic acid, to obtain Ⅻ. Ⅻ can also be cyclized from Ⅳ, followed by demethylation, reduction and the final demethylation reaction. We discussed the structure of Ⅻ and proved it by infrared spectroscopy.