A strategic study towards constructing the nine-membered azonane ring system of palhinine A via an azidoketol fragmentation reaction

• Published in: Science China. Chemistry Vol. 59; no. 9; pp. 1188 - 1196
• Main Authors: Wang, Fang-Xin, Zhang, Peng-Lin, Wang, Hui-Bin, Zhang, Guo-Biao, Fan, Chun-An
• Format: Journal Article
• Language: English
• Published: Beijing Science China Press 01.09.2016; Springer Nature B.V
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Fragmentation; 二碘化钐; 勘探战略; 反应结合; 片呐醇; 碎裂反应; 系统; fragmentation reaction; isotwistane; pinacol coupling; azonane ring; natural product synthesis; alkaloids
• ISSN: 1674-7291; 1869-1870
• DOI: 10.1007/s11426-016-0059-7

A proposed strategy for constructing the nine-membered azonane ring system embedded in the isotwistane framework of palhinine A has been preliminarily studied on the basis of an azidoketol fragmentation reaction together with a SmI2-mediated pinacol coupling. Albeit negative results for building the azonane ring scaffold via a tertiary azidoketol fragmentation, the present exploration strategically provided an endeavor to probe the synthetically challenging issue in the synthetic study of palhinine A.