Synthesis of polyacenequinones via a benzo[2,3-c]furan |
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| Affiliation: | 1. Departamento de Química, Universidad del Valle, AA 25360 Cali, Colombia;2. Escuela de Química, Universidad Industrial de Santander, 680002 Bucaramanga, Colombia;3. Departamento de Física, Universidad del Valle, AA 25360 Cali, Colombia;4. Centro de Excelencia en Nuevos Materiales (CENM), Universidad del Valle, AA 25360 Cali, Colombia;1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmans’ka Str. 5, 02660 Kyiv, Ukraine;2. Fakultät für Chemie der Universität Bielefeld, Universitätstr. 25, 33615 Bielefeld, Germany;3. Department of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39217, United States;1. Department of Pharmacognosy and Chemistry of Natural Products, Faculty of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, Athens 15771, Greece;2. Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb 10000, Croatia;3. Laboratoire de Biologie Moléculaire et Cellulaire du Cancer (LBMCC), Luxembourg;4. Natural Products Chemistry Department, National Research Center, Dokki, Cairo 12622, Egypt;5. Department of Pharmacy, College of Pharmacy, Seoul National University, Seoul 151-742, Republic of Korea |
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| Abstract: | 1,3-Bis(4-tert-butylphenyl)-4.7-diacetoxybenzo- (2,3-c)furan (3c) serves as a masked-dienophile/diene equivalent, which can elongate a 1,4-quinone by two rings. Elongation Involves a three step sequence of Diels-Alder reaction, dehydrative-aromatization. and oxidative unmasking of the dienophile. This elongation strategy has been used to sequentially convert napthoquinone to a tetracenetetrone and a hexacenetetrone. |
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