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Preparation of a key tetraene precursor for the synthesis of long acenes
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2020-02-26 , DOI: 10.1002/ejoc.201901868 Gaspard Levet 1 , Nguyen Khanh Hung 1 , Michal Šámal 2 , Jiří Rybáček 2 , Ivana Cisařová 2 , Andrej Jancarik 1, 2 , André Gourdon 1
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2020-02-26 , DOI: 10.1002/ejoc.201901868 Gaspard Levet 1 , Nguyen Khanh Hung 1 , Michal Šámal 2 , Jiří Rybáček 2 , Ivana Cisařová 2 , Andrej Jancarik 1, 2 , André Gourdon 1
Affiliation
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The tetraene 7,7-dimethoxy-2,3,5,6-tetramethylenebicyclo[2.2.1]heptane is a key compound for the preparation of a large variety of acenes protected by a carbonyl bridge. We report here a medium scale preparation in seven steps of this valuable starting material. Diels-Alder addition between 6,6-dimethyl fulvene and maleic anhydride, followed by carboxylation, ozonolysis of the double bond, reduction of the four ester group, then chlorination of the alcohol groups and dehydrochlorination give the target compound in 17% overall yield.
中文翻译：
合成长并苯的关键四烯前体的制备
四烯 7,7-二甲氧基-2,3,5,6-四亚甲基双环 [2.2.1] 庚烷是制备由羰基桥保护的多种并苯的关键化合物。我们在这里报告了这种有价值的起始材料的七个步骤的中等规模制备。6,6-二甲基富烯和马来酸酐之间进行狄尔斯-阿尔德加成，然后羧化，双键臭氧分解，四个酯基还原，然后醇基氯化和脱氯化氢得到目标化合物，总产率为17%。
更新日期：2020-02-26
中文翻译：
合成长并苯的关键四烯前体的制备
四烯 7,7-二甲氧基-2,3,5,6-四亚甲基双环 [2.2.1] 庚烷是制备由羰基桥保护的多种并苯的关键化合物。我们在这里报告了这种有价值的起始材料的七个步骤的中等规模制备。6,6-二甲基富烯和马来酸酐之间进行狄尔斯-阿尔德加成，然后羧化，双键臭氧分解，四个酯基还原，然后醇基氯化和脱氯化氢得到目标化合物，总产率为17%。
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