Asymmetric Formal Synthesis of (+)-Catharanthine via Desymmetrization of Isoquinuclidine
Although (+)-catharanthine is an attractive alkaloid for both clinical research and organic synthetic chemistry, only a limited number of approaches for its catalytic asymmetric synthesis exist. Herein, we describe a novel strategy for synthesizing a chiral intermediate of (+)-catharanthine via phos...
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| Veröffentlicht in: | Organic letters 2019-05, Vol.21 (10), p.3750-3754 |
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| container_issue | 10 |
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| container_title | Organic letters |
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| creator | Kono, Masato Harada, Shingo Nozaki, Tomoyuki Hashimoto, Yoshinori Murata, Shun-ichi Gröger, Harald Kuroda, Yusuke Yamada, Ken-ichi Takasu, Kiyosei Hamada, Yasumasa Nemoto, Tetsuhiro |
| description | Although (+)-catharanthine is an attractive alkaloid for both clinical research and organic synthetic chemistry, only a limited number of approaches for its catalytic asymmetric synthesis exist. Herein, we describe a novel strategy for synthesizing a chiral intermediate of (+)-catharanthine via phosphoric acid-catalyzed asymmetric desymmetrization of a meso-isoquinuclidine possessing a 1,3-diol unit that was synthesized by a formal amide insertion reaction. |
| doi_str_mv | 10.1021/acs.orglett.9b01198 |
| format | Article |
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| title | Asymmetric Formal Synthesis of (+)-Catharanthine via Desymmetrization of Isoquinuclidine |
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