A formal total synthesis of (+/-)-cephalotaxine using sequential N-acyliminium ion reactions |
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Authors: | Koseki Yuji Sato Hiroto Watanabe Yumi Nagasaka Tatsuo |
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Institution: | Tokyo University of Pharmacy and Life Science, School of Pharmacy, 1432-1 Horinouchi, Hachiouji, Tokyo 192-0392, Japan. |
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Abstract: | reaction: see text] Novel synthesis of cephalotaxine 1 based on tertiary N-acyliminium ion chemistry starting from alkynylamide 2 was achieved. The key steps include the preparation of pyrroloisoquinoline 4 from alkynylamide 2, the ring expansion of pyrroloisoquinoline 4 to pyrrolobenzazepine 12, and the construction of cyclopentapyrrolobenzazepine ring system 6, all of which are derived from N-acyliminium ion intermediates. |
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