Asymmetric synthesis of anthracyclinones using chiral acetal: synthesis of a new chiral AB-synthon, ()-2-bromo-6-ethynyl-6-hydroxy-5, 6, 7, 8-tetrahydro-1, 4-naphthoquinone,and its application for ()-7-deoxydaunomycinone |
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| Affiliation: | 1. Organic Chemistry Division-II (C P C Division), CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, Telangana, India;2. Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500078, Telangana, India;1. Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea;2. Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, 80 Daehakro, Buk-gu, Daegu, 41566, Republic of Korea |
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| Abstract: | A synthesis of a new chiral AB-synthon (4) for preparing the optically active anthracyclinones was attained through a stereospecific nucleophilic addition of trimethylsilylethynylmagnesium chloride to the chiral 2-tetralone-1-acetal (2). Synthesis of ()-7-deoxydaunomycinone (1c) was achieved by a regiospecific cycloaddition of4 to 4-acetoxy-8-methoxyhomophthalic anhydride (5). |
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