Synthetic studies on chartelline C: stereoselective construction of the core skeleton |
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Authors: | Kotaro Iwasaki Rentaro Kanno Toshiharu Morimoto Tohru Yamashita Satoshi Yokoshima Tohru Fukuyama |
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Affiliation: | Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan). |
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Abstract: | What a core-ker! The title synthesis was achieved using a route featuring an intramolecular Mitsunobu reaction of a nosyl amide, stereoselective construction of the β-lactam, and formation of an enamide moiety by selenoxide elimination. The stereochemistry of the alkylation for the formation of the β-lactam was controlled by a secondary hydroxy group on the ten-membered ring. SEM=2-(trimethylsilyl)ethoxymethyl; TBS=tert-butyldimethylsilyl. |
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Keywords: | imidazole Mitsunobu reaction natural products spiro β‐lactams total synthesis |
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