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CC BY-NC-ND 4.0 · SynOpen 2022; 06(04): 306-311
DOI: 10.1055/a-1952-4557
paper

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

Shen Tan
a   Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong, 510632, P. R. of China
,
Ping Lan
a   Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong, 510632, P. R. of China
,
Martin G. Banwell  ∗
a   Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong, 510632, P. R. of China
b   Guangdong Key Laboratory for Research and the Development of Natural Drugs, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang, Guangdong 524023, P. R. of China
,
Lorenzo V. White∗
a   Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong, 510632, P. R. of China
› InstitutsangabenWe thank the National Natural Science Foundation of China (Grant Nos. 22250410258 and 22250410259) and the Ministry of Science and Technology of the People’s Republic of China for financial support.
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Abstract

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.

Key Words

1,2-addition - α,β-annulation - cross-coupling - cyclohexenone - enantiomerically pure - α-iodination - quinic acid

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1952-4557. Included are an outline of the general synthetic protocols employed in this study, plots derived from the single-crystal X-ray analyses of compound 8, the N-hydroxy derivative of compound 12 and of compound 14 together with copies of the 1H and 13C NMR spectra of compounds 2–6, 8, 9, 11, 12 and 14.
  • Supporting Information


Publikationsverlauf

Eingereicht: 19. September 2022

Angenommen nach Revision: 28. September 2022

Accepted Manuscript online:
28. September 2022

Artikel online veröffentlicht:
21. November 2022

© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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