An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry |
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| Institution: | 1. Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia;2. CSIRO Division of Molecular Science, Clayton, VIC 3165, Australia;1. Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan;2. South Ehime Fisheries Research Center, 1289-1 Funakoshi, Ainan, Ehime 798-4292, Japan;1. School of Civil, Environmental and Architectural Engineering, Korea University, Anam-dong, Seongbuk-gu, Seoul 136-701, Republic of Korea;2. Department of Environmental Engineering, Kumoh National Institute of Technology, 61 Daehak-ro, Gumi, Gyungbuk 730-701, Republic of Korea;1. Department of Chemical Enginnering and Biotechnology, National Taipei University of Technology, Taipei 10608, Taiwan (ROC);2. Department of Biochemistry, College of Medicine, Taipei Medical University, No. 250, Wu-xing Street, Taipei 110, Taiwan (ROC);1. Laboratory of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Box 183, Dschang, Cameroon;2. School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, I-62032 Camerino, Italy;3. Laboratoire de Pharmacognosie, UFR des Sciences de Santé (Pharmacie), EA 4267 (FDE/UFC), Université de Bourgogne, 7, Boulevard Jeanne d’Arc, BP 87900, 21079 Dijon Cedex, France;4. School of Pharmacy, Physiology Division, University of Camerino, Via Gentile III da Varano, I-62032 Camerino, Italy |
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| Abstract: | The title natural product (−)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-β to give triol (1R,2R)-1-(3′,5′-dimethoxy-4′-methoxymethoxyphenyl)-2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2′ and C-3′. |
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