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Total synthesis of the tricyclic humulanolide wilfolide B
Affiliation:1. Department of Chemical and Biological Sciences, Faculty of Science, Japan Women’s University, 2-8-1 Mejirodai, Bunkyo-ku, Tokyo 112-8681, Japan;2. School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan;1. Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, China;2. State Key Laboratory of Stress Biology for Arid Areas, Northwest A&F University, Yangling, Shaanxi, China;3. The College of Plant Protection, Northwest A&F University, China;4. Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling, Shaanxi 712100, China;1. Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;2. Academy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India;1. Department of Chemistry, Department of Biochemistry, Vanderbilt University, Nashville, TN 37232-6600, USA;2. Department of Pharmacology, Vanderbilt Center for Neuroscience Drug Discovery, Vanderbilt University, Nashville, TN 37232-6600, USA;1. Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal - 462 066, Madhya Pradesh, India;2. Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia - 741 246, West Bengal, India
Abstract:
The first total synthesis of tricyclic humulanolide wilfolide B was achieved. The synthetic strategy involved: i) radical cyclization with samarium(II) iodide to construct the bicyclic lactone from an acyclic compound, and ii) ring-closing metathesis to build the eight-membered ring by connecting two side chains, thus completing the tricyclic framework.
Keywords:Wilfolide B  Radical cyclization  Ring-closing metathesis  Total synthesis
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