从酰基亚硝基狄尔斯-阿尔德环加成物简洁合成2-氨基双环[3.1.0]己烷-2,6-二羧酸（LY354740）的4-酰氨基类似物。
concise synthesis of 4-acylamino analogues of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acids (LY354740) from an acylnitroso Diels-Alder cycloadduct.
作者信息
Lee Wenlin, Miller Marvin J
机构信息
Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA.
出版信息
J Org Chem. 2004 Jun 25;69(13):4516-9. doi: 10.1021/jo0495034.
Concise total syntheses of 4-acylamino analogues of LY354740 were accomplished employing an N-Boc acylnitroso Diels-Alder cycloadduct as the starting material. The syntheses involved N-O bond cleavage, oxidation, intermolecular cyclopropanation, Bucherer-Bergs reaction, hydrolysis, and regioselective acylation with a temporary copper chelate. The synthesis of an optically active compound was also achieved.
以N - Boc酰基亚硝基狄尔斯 - 阿尔德环加成物为起始原料，完成了LY354740的4 - 酰氨基类似物的简洁全合成。合成过程包括N - O键断裂、氧化、分子间环丙烷化、布赫尔 - 贝格斯反应、水解以及用临时铜螯合物进行区域选择性酰化。还实现了一种光学活性化合物的合成。
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