Total synthesis of ent-dihydrocorynantheol by using a proline-catalyzed asymmetric addition reaction |
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| Authors: | Itoh Takashi Yokoya Masashi Miyauchi Keiko Nagata Kazuhiro Ohsawa Akio |
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| Institution: | School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. itoh-t@pharm.showa-u.ac.jp |
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| Abstract: | reaction: see text] 9-Tosyl-3,4-dihydro-beta-carboline reacted with 3-ethyl-3-buten-2-one in the presence of (S)-proline to give (3R,12bR)-3-ethyl-12-tosyl-3,4,6,7,8,9,10,11,12,12b-decahydro-1H-indolo2,3-a]quinolizin-2-one in complete enantio- and diastereoselectivity. The compound thus obtained was readily transformed to ent-dihydrocorynantheol in three steps. |
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