Enantioselective Formal Synthesis of (-)-Catharanthine through Enzyme-Catalyzed Desymmetrization of a meso -Azabicyclo [2.2.2]octane
Ikeda K, Harada S, Hashimoto Y, Homma H, Kono M, Zumbrägel N, Gröger H, Nemoto T (2023)
Synlett.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Ikeda, Kotaro;
Harada, Shingo;
Hashimoto, Yoshinori;
Homma, Haruka;
Kono, Masato;
Zumbrägel, NadineUniBi 
;
Gröger, HaraldUniBi;
Nemoto, Tetsuhiro
;
Gröger, HaraldUniBi;
Nemoto, TetsuhiroAbstract / Bemerkung
Iboga-type indole alkaloids are a promising compound group of potentially effective drugs. The common indole-fused pentacyclic skeleton is composed of an isoquinuclidine, and both enantiomers of this architecture are naturally present. In this study, we used enzymatic desymmetrization to obtain an optically active isoquinuclidine possessing four chiral carbon centers from a prochiral diester in one step. In addition, we synthesized a pentacyclic intermediate for catharanthine in an enantioenriched form through the late-stage construction of the common Iboga scaffold.
Stichworte
enzymatic desymmetrization;
desymmetrization;
carbenes;
enantioselective;
synthesis;
alkaloids;
isoquinuclidines
Erscheinungsjahr
2023
Zeitschriftentitel
Synlett
ISSN
0936-5214
eISSN
1437-2096
Page URI
https://pub.uni-bielefeld.de/record/2980004
Zitieren
Ikeda K, Harada S, Hashimoto Y, et al. Enantioselective Formal Synthesis of (-)-Catharanthine through Enzyme-Catalyzed Desymmetrization of a meso -Azabicyclo [2.2.2]octane. Synlett. 2023.
Ikeda, K., Harada, S., Hashimoto, Y., Homma, H., Kono, M., Zumbrägel, N., Gröger, H., et al. (2023). Enantioselective Formal Synthesis of (-)-Catharanthine through Enzyme-Catalyzed Desymmetrization of a meso -Azabicyclo [2.2.2]octane. Synlett. https://doi.org/10.1055/a-2086-0690
Ikeda, Kotaro, Harada, Shingo, Hashimoto, Yoshinori, Homma, Haruka, Kono, Masato, Zumbrägel, Nadine, Gröger, Harald, and Nemoto, Tetsuhiro. 2023. “Enantioselective Formal Synthesis of (-)-Catharanthine through Enzyme-Catalyzed Desymmetrization of a meso -Azabicyclo [2.2.2]octane”. Synlett.
Ikeda, K., Harada, S., Hashimoto, Y., Homma, H., Kono, M., Zumbrägel, N., Gröger, H., and Nemoto, T. (2023). Enantioselective Formal Synthesis of (-)-Catharanthine through Enzyme-Catalyzed Desymmetrization of a meso -Azabicyclo [2.2.2]octane. Synlett.
Ikeda, K., et al., 2023. Enantioselective Formal Synthesis of (-)-Catharanthine through Enzyme-Catalyzed Desymmetrization of a meso -Azabicyclo [2.2.2]octane. Synlett.
K. Ikeda, et al., “Enantioselective Formal Synthesis of (-)-Catharanthine through Enzyme-Catalyzed Desymmetrization of a meso -Azabicyclo [2.2.2]octane”, Synlett, 2023.
Ikeda, K., Harada, S., Hashimoto, Y., Homma, H., Kono, M., Zumbrägel, N., Gröger, H., Nemoto, T.: Enantioselective Formal Synthesis of (-)-Catharanthine through Enzyme-Catalyzed Desymmetrization of a meso -Azabicyclo [2.2.2]octane. Synlett. (2023).
Ikeda, Kotaro, Harada, Shingo, Hashimoto, Yoshinori, Homma, Haruka, Kono, Masato, Zumbrägel, Nadine, Gröger, Harald, and Nemoto, Tetsuhiro. “Enantioselective Formal Synthesis of (-)-Catharanthine through Enzyme-Catalyzed Desymmetrization of a meso -Azabicyclo [2.2.2]octane”. Synlett (2023).
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Suchen in
Google Scholar