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First total syntheses of (+)-7-deoxynogarol and (+)-7-con-o-methylnogarol
Institution:1. Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand;2. Chulabhorn Graduate Institute and Center of Excellence on Environmental Health and Toxicology (EHT), CHE, Ministry of Education, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand;3. Laboratory of Natural Products Chemistry, Faculty of Science and Technology, Phuket Rajabhat University, Phuket 83000, Thailand;1. State Key Laboratory of Functions and Applications of Medicinal Plants & School of Pharmaceutical Sciences, Guizhou Medical University, 550004 Guiyang, China;2. Key Lab of Green Chemistry and Technology, Ministry of Education College of Chemistry, Sichuan University, 610064 Chengdu, China;1. School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, PR China;2. School of Pharmacy, Liaoning University of Traditional Chinese Medicine, Dalian 116600, PR China
Abstract:The first total syntheses of (+)-7-deoxynogarol (2) and (+)-7-con-O-methylnogarol (3), the notable members of nogalamycin congeners, were achieved employing the Diels-Alder reaction of the highly functionalized dienes (11 and 20) with the (+)-naphthoquinone (6), the CDEF-ring system of nogalamycin congeners, as a key synthetic step.
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