Otani Takashi, Tamai Yumiko, Seki Kazunori, Kikuchi Tomohiro, Miyazawa Taiichiro, Saito Takao
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan.
Org Biomol Chem. 2015 Jun 7;13(21):5875-9. doi: 10.1039/c5ob00503e.
We describe the stereoselective synthesis of polyring-fused heterocyclic compounds based on diene-transmissive hetero-Diels-Alder reactions utilizing β,γ-unsaturated α-keto esters. This protocol involves the initial endo- or exo-selective Diels-Alder (DA) reactions with electron-rich dienophiles, methylenation of the ester carbonyl groups with the Tebbe reagent, and a stereoselective second DA reaction with electron-deficient dienophiles. The use of enantioselective DA reactions in the initial reaction enables access to chiral polyring-fused heterocyclic compounds with multiple chiral centres.
我们描述了基于利用β,γ-不饱和α-酮酯的二烯传递型杂Diels-Alder反应的多环稠合杂环化合物的立体选择性合成。该方法包括首先与富电子亲双烯体进行内型或外型选择性Diels-Alder（DA）反应，用Tebbe试剂对酯羰基进行亚甲基化，以及与缺电子亲双烯体进行立体选择性的第二次DA反应。在初始反应中使用对映选择性DA反应能够获得具有多个手性中心的手性多环稠合杂环化合物。
