The synthesis of a natural product family: from debromoisolaurinterol to the aplysins |
| |
| Affiliation: | 1. Department of Chemistry, The University, Southampton S017 1BJ, UK;2. Medicinal Chemistry 2, GlaxoWellcome Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts SG1 2NY, UK;1. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok, Russia;2. Far Eastern Federal University, Vladivostok, Russia;1. N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russia;2. S.N. Winogradsky Institute of Microbiology, Russian Academy of Sciences, Moscow 117312, Russia;1. Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, P.R. China;1. Department of Life Science and Technology, School of Life Science and Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan;2. Graduate School of Science and Technology, Kumamoto University, 2-39-1 Kurokami, Chuo-ku, Kumamoto 860-8555, Japan;3. Division of Biomaterials, Institute of Industrial Nanomaterials (IINa), Kumamoto University, 2-39-1 Kurokami, Chuo-ku, Kumamoto 860–8555, Japan;4. Faculty of Advanced Science and Technology (FAST), Kumamoto University, 2-39-1 Kurokami, Chuo-ku, Kumamoto 860-8555, Japan |
| |
| Abstract: | Total syntheses of (±)-aplysin 1, (±)-debromoaplysin 2, (±)-isoaplysin 3, (±)-aplysinol 4, (±)-debromoaplysinol 5, (±)-aplysinal 6, (±)-isolaurinterol 7 and (±)-debromoisolaurinterol 8 are described. Key features are a diastereoselective, sulfur mediated radical cyclisation of diene 12 to give 35; a new radical to polar crossover sequence mediated by Bu3Sn that transforms diene 12 into (±)-debromoisolaurinterol 8; and a series of biomimetic cyclisation and oxidation reactions. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
