Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid
The naturally abundant, enantiomerically pure cyclitol quinic acid has been converted into a synthetically useful enone in nearly quantitative yield using the operationally straightforward and reproducible protocols reported herein. The latter compound, which was obtained in multigram quantities, en...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Georg Thieme Verlag KG
2022-11-01
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| Series: | SynOpen |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/a-1952-4557 |
| _version_ | 1811189205140766720 |
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| author | Shen Tan Ping Lan Martin G. Banwell Lorenzo V. White |
| author_facet | Shen Tan Ping Lan Martin G. Banwell Lorenzo V. White |
| author_sort | Shen Tan |
| collection | DOAJ |
| description | The naturally abundant, enantiomerically pure cyclitol quinic acid has been converted into a synthetically useful enone in nearly quantitative yield using the operationally straightforward and reproducible protocols reported herein. The latter compound, which was obtained in multigram quantities, engages in a diastereoselective 1,2-addition reaction with a hydrazone-based nucleophile. Furthermore, a readily derived α-iodoenone participates in both cross-coupling and α,β-annulation reactions. The results reported here emphasize that the now practically accessible cyclohexenones are useful, enantiomerically pure building blocks for organic synthesis. |
| first_indexed | 2024-04-11T14:31:57Z |
| format | Article |
| id | doaj.art-6278eda747c24214980921800492c024 |
| institution | Directory Open Access Journal |
| issn | 2509-9396 |
| language | English |
| last_indexed | 2024-04-11T14:31:57Z |
| publishDate | 2022-11-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | SynOpen |
| spelling | doaj.art-6278eda747c24214980921800492c0242022-12-22T04:18:33ZengGeorg Thieme Verlag KGSynOpen2509-93962022-11-01060430631110.1055/a-1952-4557Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic AcidShen Tan0Ping Lan1Martin G. Banwell2Lorenzo V. White3Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan UniversityInstitute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan UniversityInstitute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan UniversityInstitute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan UniversityThe naturally abundant, enantiomerically pure cyclitol quinic acid has been converted into a synthetically useful enone in nearly quantitative yield using the operationally straightforward and reproducible protocols reported herein. The latter compound, which was obtained in multigram quantities, engages in a diastereoselective 1,2-addition reaction with a hydrazone-based nucleophile. Furthermore, a readily derived α-iodoenone participates in both cross-coupling and α,β-annulation reactions. The results reported here emphasize that the now practically accessible cyclohexenones are useful, enantiomerically pure building blocks for organic synthesis.http://www.thieme-connect.de/DOI/DOI?10.1055/a-1952-45571,2-additionα,β-annulationcross-couplingcyclohexenoneenantiomerically pureα-iodinationquinic acid |
| spellingShingle | Shen Tan Ping Lan Martin G. Banwell Lorenzo V. White Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid SynOpen 1,2-addition α,β-annulation cross-coupling cyclohexenone enantiomerically pure α-iodination quinic acid |
| title | Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid |
| title_full | Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid |
| title_fullStr | Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid |
| title_full_unstemmed | Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid |
| title_short | Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid |
| title_sort | practical multigram preparation of synthetically useful enantiomerically pure building blocks from quinic acid |
| topic | 1,2-addition α,β-annulation cross-coupling cyclohexenone enantiomerically pure α-iodination quinic acid |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/a-1952-4557 |
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