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Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid | |
article | |
Shen Tan1  Ping Lan1  Martin G. Banwell1  Lorenzo V. White1  | |
[1] Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University;Guangdong Key Laboratory for Research and the Development of Natural Drugs, The Marine Biomedical Research Institute, Guangdong Medical University | |
关键词: 1; 2-addition; α; β-annulation; cross-coupling; cyclohexenone; enantiomerically pure; α-iodination; quinic acid; | |
DOI : 10.1055/a-1952-4557 | |
学科分类:精神健康和精神病学 | |
来源: Thieme | |
【 摘 要 】
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.
【 授权许可】
CC BY|CC BY-NC-ND
【 预 览 】
Files | Size | Format | View |
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RO202307130003276ZK.pdf | 470KB | download |