Skeletal contraction: A novel strategy to access multisubstituted cyclobutane
The polysubstituted and spirocyclic cyclobutanes were efficiently constructed by the utilization of a novel skeletal contraction strategy which only took one-step synthesis from the readily accessible pyrrolidines. The mechanistic studies indicated that a key intermediate N-aminated pyrrolidine was...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2022-02-01
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| Series: | Green Synthesis and Catalysis |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666554921001101 |
| _version_ | 1818138444170264576 |
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| author | Chunfa Xu V.U. Bhaskara Rao Fen-Er Chen |
| author_facet | Chunfa Xu V.U. Bhaskara Rao Fen-Er Chen |
| author_sort | Chunfa Xu |
| collection | DOAJ |
| description | The polysubstituted and spirocyclic cyclobutanes were efficiently constructed by the utilization of a novel skeletal contraction strategy which only took one-step synthesis from the readily accessible pyrrolidines. The mechanistic studies indicated that a key intermediate N-aminated pyrrolidine was formed initially and subsequent extrusion of a nitrogen via a radical pathway completed the transformation. This practical methodology was further highlighted by the concise, formal synthesis of the cytotoxic natural product piperarborenine B. |
| first_indexed | 2024-12-11T10:12:17Z |
| format | Article |
| id | doaj.art-6c05ffb17cc14618b40d64aa0bd8f83f |
| institution | Directory Open Access Journal |
| issn | 2666-5549 |
| language | English |
| last_indexed | 2024-12-11T10:12:17Z |
| publishDate | 2022-02-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Synthesis and Catalysis |
| spelling | doaj.art-6c05ffb17cc14618b40d64aa0bd8f83f2022-12-22T01:11:42ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492022-02-013113Skeletal contraction: A novel strategy to access multisubstituted cyclobutaneChunfa Xu0V.U. Bhaskara Rao1Fen-Er Chen2Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China; Corresponding authors.Department of Chemical Biology, Max Planck Institute for Molecular Physiology, Otto-Hahn Street 11, Dortmund 44227, GermanyInstitute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China; Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China; Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Fudan University, Shanghai 200433, China; Corresponding authors. Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou, 350108, China.The polysubstituted and spirocyclic cyclobutanes were efficiently constructed by the utilization of a novel skeletal contraction strategy which only took one-step synthesis from the readily accessible pyrrolidines. The mechanistic studies indicated that a key intermediate N-aminated pyrrolidine was formed initially and subsequent extrusion of a nitrogen via a radical pathway completed the transformation. This practical methodology was further highlighted by the concise, formal synthesis of the cytotoxic natural product piperarborenine B.http://www.sciencedirect.com/science/article/pii/S2666554921001101CyclobutaneSkeletal contractionHypervalent iodinePyrrolidinesPiperarboreine B |
| spellingShingle | Chunfa Xu V.U. Bhaskara Rao Fen-Er Chen Skeletal contraction: A novel strategy to access multisubstituted cyclobutane Green Synthesis and Catalysis Cyclobutane Skeletal contraction Hypervalent iodine Pyrrolidines Piperarboreine B |
| title | Skeletal contraction: A novel strategy to access multisubstituted cyclobutane |
| title_full | Skeletal contraction: A novel strategy to access multisubstituted cyclobutane |
| title_fullStr | Skeletal contraction: A novel strategy to access multisubstituted cyclobutane |
| title_full_unstemmed | Skeletal contraction: A novel strategy to access multisubstituted cyclobutane |
| title_short | Skeletal contraction: A novel strategy to access multisubstituted cyclobutane |
| title_sort | skeletal contraction a novel strategy to access multisubstituted cyclobutane |
| topic | Cyclobutane Skeletal contraction Hypervalent iodine Pyrrolidines Piperarboreine B |
| url | http://www.sciencedirect.com/science/article/pii/S2666554921001101 |
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