title: Total Synthesis of Notoamides F, I, and R and Sclerotiamide.
abstract: The total synthesis of the natural indole alkaloids (+)-notoamide F, I, and R and (-)-sclerotiamide is described. The four heptacyclic compounds were synthesized in 10-12 steps in a convergent and highly stereoselective manner from the readily available Seebach acetal. Key steps of the synthesis include a stereoselective oxidative aza-Prins cyclization to construct the bicyclo[2.2.2]diazaoctane, and a cobalt-catalyzed radical cycloisomerization to create the cyclohexenyl ring.
authors.affiliation: Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P.R. China.
authors.forename: Benxiang
authors.initials: B
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P.R. China.
authors.forename: Weifeng
authors.initials: W
authors.lastname: Zheng
authors.affiliation: Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P.R. China.
authors.forename: Xiaoqing
authors.initials: X
authors.lastname: Wang
authors.affiliation: Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P.R. China. sundeqian@sioc.ac.cn.
authors.forename: Deqian
authors.initials: D
authors.lastname: Sun
authors.affiliation: Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P.R. China. clig@mail.sioc.ac.cn.|School of Chemical Engineering, Ningbo University of Technology, 89 Cuibai Road, Ningbo, 315016, P.R. China. clig@mail.sioc.ac.cn.
authors.forename: Chaozhong
authors.identifier: 0000-0002-5135-9115
authors.initials: C
authors.lastname: Li
keywords: cyclization; indole alkaloids; natural products; radicals; total synthesis