Synthetic Study of Dragmacidin E: Enantioselective Construction of the Seven-Membered Ring-Fused Indole Skeleton with Contiguous Stereocenters

Choi D, Takahashi N, Maruoka H, Harada S, Nastke A, Gröger H, Nemoto T (2023)
Journal of Organic Chemistry, The .

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Autor*in
Choi, Dongil; Takahashi, Noa; Maruoka, Haruka; Harada, Shingo; Nastke, AlinaUniBi; Gröger, HaraldUniBi; Nemoto, Tetsuhiro
Abstract / Bemerkung
We developed an enantioselective synthetic method of constructing a seven-membered ring-fused indole skeleton with contiguous stereocenters for the synthesis of dragmacidin E. Introduction of chirality at the benzylic position was achieved by Ir-catalyzed asymmetric hydrogenation. After construction of the tricyclic molecular framework using Pd-catalyzed cascade cyclization, the tetrasubstituted carbon center was created using the Ag nitrene-mediated C-H amination reaction. The developed method provided access to the functionalized seven-membered ring-fused indole skeleton with a hydroxymethyl branch in the tetrasubstituted carbon.
Erscheinungsjahr
2023
Zeitschriftentitel
Journal of Organic Chemistry, The
eISSN
1520-6904
Page URI
https://pub.uni-bielefeld.de/record/2968666

Zitieren

Choi D, Takahashi N, Maruoka H, et al. Synthetic Study of Dragmacidin E: Enantioselective Construction of the Seven-Membered Ring-Fused Indole Skeleton with Contiguous Stereocenters. Journal of Organic Chemistry, The . 2023.
Choi, D., Takahashi, N., Maruoka, H., Harada, S., Nastke, A., Gröger, H., & Nemoto, T. (2023). Synthetic Study of Dragmacidin E: Enantioselective Construction of the Seven-Membered Ring-Fused Indole Skeleton with Contiguous Stereocenters. Journal of Organic Chemistry, The . https://doi.org/10.1021/acs.joc.2c02216
Choi, Dongil, Takahashi, Noa, Maruoka, Haruka, Harada, Shingo, Nastke, Alina, Gröger, Harald, and Nemoto, Tetsuhiro. 2023. “Synthetic Study of Dragmacidin E: Enantioselective Construction of the Seven-Membered Ring-Fused Indole Skeleton with Contiguous Stereocenters”. Journal of Organic Chemistry, The .
Choi, D., Takahashi, N., Maruoka, H., Harada, S., Nastke, A., Gröger, H., and Nemoto, T. (2023). Synthetic Study of Dragmacidin E: Enantioselective Construction of the Seven-Membered Ring-Fused Indole Skeleton with Contiguous Stereocenters. Journal of Organic Chemistry, The .
Choi, D., et al., 2023. Synthetic Study of Dragmacidin E: Enantioselective Construction of the Seven-Membered Ring-Fused Indole Skeleton with Contiguous Stereocenters. Journal of Organic Chemistry, The .
D. Choi, et al., “Synthetic Study of Dragmacidin E: Enantioselective Construction of the Seven-Membered Ring-Fused Indole Skeleton with Contiguous Stereocenters”, Journal of Organic Chemistry, The , 2023.
Choi, D., Takahashi, N., Maruoka, H., Harada, S., Nastke, A., Gröger, H., Nemoto, T.: Synthetic Study of Dragmacidin E: Enantioselective Construction of the Seven-Membered Ring-Fused Indole Skeleton with Contiguous Stereocenters. Journal of Organic Chemistry, The . (2023).
Choi, Dongil, Takahashi, Noa, Maruoka, Haruka, Harada, Shingo, Nastke, Alina, Gröger, Harald, and Nemoto, Tetsuhiro. “Synthetic Study of Dragmacidin E: Enantioselective Construction of the Seven-Membered Ring-Fused Indole Skeleton with Contiguous Stereocenters”. Journal of Organic Chemistry, The (2023).

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