Toward the Synthesis of Yuzurimine-Type Alkaloids: Stereoselective Construction of the Heterocyclic Portions of Deoxyyuzurimine and Macrodaphnine
- Ichiro Hayakawa*Ichiro Hayakawa*E-mail: [email protected]Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, JapanMore by Ichiro Hayakawa,
- Ryosuke NagataniRyosuke NagataniDivision of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, JapanMore by Ryosuke Nagatani,
- Masaki IkedaMasaki IkedaDivision of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, JapanMore by Masaki Ikeda,
- Dong-eun YooDong-eun YooDivision of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, JapanMore by Dong-eun Yoo,
- Keita SaitoKeita SaitoDepartment of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571, JapanMore by Keita Saito,
- Hideo KigoshiHideo KigoshiDepartment of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571, JapanMore by Hideo Kigoshi, and
- Akira Sakakura*Akira Sakakura*E-mail: [email protected]Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, JapanMore by Akira Sakakura
Abstract
The heterocyclic portions of yuzurimine-type alkaloids, such as deoxyyuzurimine and macrodaphnine, were synthesized by using a stereoselective hydroboration–oxidation reaction to install the C20 methyl group, the intramolecular Mitsunobu reaction to construct the E-ring portion, and the intramolecular SN2 reaction to construct the F-ring portion as key steps.
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- Lian-Dong Guo, Jingping Hu, Yan Zhang, Wentong Tu, Yue Zhang, Fan Pu, Jing Xu. Enantioselective Total Synthesis of (−)-Caldaphnidine O via a Radical Cyclization Cascade. Journal of the American Chemical Society 2019, 141 (33) , 13043-13048. https://doi.org/10.1021/jacs.9b07558
- Lian-Dong Guo, Yan Zhang, Jingping Hu, Chengqing Ning, Heyifei Fu, Yuye Chen, Jing Xu. Asymmetric total synthesis of yuzurimine-type Daphniphyllum alkaloid (+)-caldaphnidine J. Nature Communications 2020, 11 (1) https://doi.org/10.1038/s41467-020-17350-x
- Jiaxin Zhong, Haibing He, Shuanhu Gao. Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids. Organic Chemistry Frontiers 2019, 6 (22) , 3781-3785. https://doi.org/10.1039/C9QO01111K