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Synthesis 2024; 56(13): 2059-2065
DOI: 10.1055/s-0043-1774861
DOI: 10.1055/s-0043-1774861
paper
Syntheses of 7a-Substituted Pyrrolizidine Derivatives via Stereocontrolled Anionic Cyclization
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
Publikationsverlauf
Eingereicht: 02. Februar 2024
Angenommen nach Revision: 15. April 2024
Artikel online veröffentlicht:
06. Mai 2024
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