Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid

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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