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DOI: 10.1055/s-0043-1774861
Syntheses of 7a-Substituted Pyrrolizidine Derivatives via Stereocontrolled Anionic Cyclization
Autoren
This work is supported by the National Natural Science Foundation of China (Grant Nos. 52172174, 51872002, and 21771001), the Key Research and Development Projects in Anhui Province (202004a07020026), and the Program of Anhui Scientific and Technical Leaders Reserve Candidates (2018RH168).
Dedicated to Prof. Dr. Jun-Da Cen on the occasion of his 60th birthday.
Abstract
Starting from inexpensive proline and epichlorohydrin, a pivotal stereocontrolled anionic cyclization reaction paves the way for a robust and adaptable methodology to produce stereoisomers of 7a-substituted pyrrolizidine derivatives. This process yields intriguing 7a-hydroxymethyl pyrrolizidine derivatives, among them valuable trans-(2-fluorohexahydro-1H-pyrrolizin-7a-yl)methanol, which is attainable through multiple steps.
Key words
pyrrolizidine alkaloids - 7a-substituted pyrrolizidine - stereocontrolled synthesis - anionic cyclization - total synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1774861.
- Supporting Information (PDF) (opens in new window)
Publikationsverlauf
Eingereicht: 02. Februar 2024
Angenommen nach Revision: 15. April 2024
Artikel online veröffentlicht:
06. Mai 2024
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References
- 1 Moreira R, Pereira DM, Valentão P, Andrade PB. Int. J. Mol. Sci. 2018; 19: 1668
- 2 Robertson J, Stevens K. Nat. Prod. Rep. 2017; 34: 62
- 3 Schramm S, Köhler N, Rozhon W. Molecules 2019; 24: 498
- 4 Evans DeWald L, Starr C, Butters T, Treston A, Warfield KL. Antiviral Res. 2020; 184: 104881
- 5 Horne G. Iminosugars: Therapeutic Applications and Synthetic Considerations . In Carbohydrates as Drugs . Seeberger PH, Rademacher C. Topics in Medicinal Chemistry 12; Springer International Publishing; Cham: 2014: 23-51
- 6 Horne G, Wilson FX, Tinsley J, Williams DH, Storer R. Drug Discovery Today 2011; 16: 107
- 7 Martin O. Ann. Pharm. Fr. 2007; 65: 5
- 8 Nash RJ, Kato A, Yu C.-Y, Fleet GW. Future Med. Chem. 2011; 3: 1513
- 9 Wei X, Ruan W, Vrieling K. Molecules 2021; 26: 1970
- 10 Chen Y.-L, Leguijt R, Redlich H. Synthesis 2006; 2242
- 11 Chen Y.-L, Redlich H, Bergander K, Fröhlich R. Org. Biomol. Chem. 2007; 5: 3330
- 12 Ratmanova NK, Andreev IA, Leontiev AV, Momotova D, Novoselov AM, Ivanova OA, Trushkov IV. Tetrahedron 2020; 76: 131031
- 13 Wang H, Chi L, Yu F, Dai H, Gao C, Si X, Wang Z, Liu L, Zheng J, Shan L, Liu H, Zhang Q. Eur. J. Med. Chem. 2023; 249: 115124
- 14 Wang X, Allen S, Blake JF, Bowcut V, Briere DM, Calinisan A, Dahlke JR, Fell JB, Fischer JP, Gunn RJ, Hallin J, Laguer J, Lawson JD, Medwid J, Newhouse B, Nguyen P, O’Leary JM, Olson P, Pajk S, Rahbaek L, Rodriguez M, Smith CR, Tang TP, Thomas NC, Vanderpool D, Vigers GP, Christensen JG, Marx MA. J. Med. Chem. 2022; 65: 3123
- 15 Li D, Layton ME, Roecker AJ, Egbertson M, Jones KL. G, Wang X, Peng X. (Merck Sharp & Dohme Corp.) WO2015080988A1, 2015
- 16 Wang X, Burns AC, Christensen JG, Ketcham JM, Lawson JD, Marx MA, Smith CR, Allen S, Blake JF, Chicarelli MJ, Dahlke JR, Dai D, Fell JB, Fischer JP, Mejia MJ, Newhouse B, Nguyen P, O’Leary JM, Pajk S, Rodriguez ME, Savechenkov P, Tang TP, Vigers GP. A, Zhao Q. (Mirati Therapeutics INC, Array Biopharma INC) WO2021041671A1, 2021
- 17 Burns NZ, Baran PS, Hoffmann RW. Angew. Chem. Int. Ed. 2009; 48: 2854
- 18 Guo W, Gharbaoui T, Lizza JR, Meng F, Wang Y, Xin M, Chen Y, Li J, Chen C.-Y. Org. Process Res. Dev. 2022; 26: 2839
- 19 Seebach D, Sting AR, Hoffmann M. Angew. Chem. Int. Ed. 1996; 35: 2708