Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (−)-gala-Quercitol Starting from the Naturally Abundant (−)-Shikimic Acid

[Image: see text] Efficient and highly stereoselective syntheses of (+)-proto-quercitol and (−)-gala-quercitol starting from the naturally abundant (−)-shikimic acid were described in this article. (−)-Shikimic acid was first converted to the key intermediate by eight steps in 53% yield. It was then...

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Autores principales: Zhu, Xing-Liang, Wang, Lei, Luo, Yong-Qiang, He, Yun-Gang, Li, Feng-Lei, Sun, Mian-Mian, Liu, Shi-Ling, Shi, Xiao-Xin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7003206/
https://www.ncbi.nlm.nih.gov/pubmed/32039317
http://dx.doi.org/10.1021/acsomega.9b02986
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author Zhu, Xing-Liang
Wang, Lei
Luo, Yong-Qiang
He, Yun-Gang
Li, Feng-Lei
Sun, Mian-Mian
Liu, Shi-Ling
Shi, Xiao-Xin
author_facet Zhu, Xing-Liang
Wang, Lei
Luo, Yong-Qiang
He, Yun-Gang
Li, Feng-Lei
Sun, Mian-Mian
Liu, Shi-Ling
Shi, Xiao-Xin
author_sort Zhu, Xing-Liang
collection PubMed
description [Image: see text] Efficient and highly stereoselective syntheses of (+)-proto-quercitol and (−)-gala-quercitol starting from the naturally abundant (−)-shikimic acid were described in this article. (−)-Shikimic acid was first converted to the key intermediate by eight steps in 53% yield. It was then converted to (+)-proto-quercitol by three steps in 78% yield and was also converted to (−)-gala-quercitol by five steps in 63% yield. In summary, (+)-proto-quercitol and (−)-gala-quercitol were synthesized from (−)-shikimic acid by 11 and 13 steps in 41 and 33% overall yields, respectively.
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spelling pubmed-70032062020-02-07 Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (−)-gala-Quercitol Starting from the Naturally Abundant (−)-Shikimic Acid Zhu, Xing-Liang Wang, Lei Luo, Yong-Qiang He, Yun-Gang Li, Feng-Lei Sun, Mian-Mian Liu, Shi-Ling Shi, Xiao-Xin ACS Omega [Image: see text] Efficient and highly stereoselective syntheses of (+)-proto-quercitol and (−)-gala-quercitol starting from the naturally abundant (−)-shikimic acid were described in this article. (−)-Shikimic acid was first converted to the key intermediate by eight steps in 53% yield. It was then converted to (+)-proto-quercitol by three steps in 78% yield and was also converted to (−)-gala-quercitol by five steps in 63% yield. In summary, (+)-proto-quercitol and (−)-gala-quercitol were synthesized from (−)-shikimic acid by 11 and 13 steps in 41 and 33% overall yields, respectively. American Chemical Society 2020-01-21 /pmc/articles/PMC7003206/ /pubmed/32039317 http://dx.doi.org/10.1021/acsomega.9b02986 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Zhu, Xing-Liang
Wang, Lei
Luo, Yong-Qiang
He, Yun-Gang
Li, Feng-Lei
Sun, Mian-Mian
Liu, Shi-Ling
Shi, Xiao-Xin
Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (−)-gala-Quercitol Starting from the Naturally Abundant (−)-Shikimic Acid
title Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (−)-gala-Quercitol Starting from the Naturally Abundant (−)-Shikimic Acid
title_full Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (−)-gala-Quercitol Starting from the Naturally Abundant (−)-Shikimic Acid
title_fullStr Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (−)-gala-Quercitol Starting from the Naturally Abundant (−)-Shikimic Acid
title_full_unstemmed Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (−)-gala-Quercitol Starting from the Naturally Abundant (−)-Shikimic Acid
title_short Efficient and Highly Stereoselective Syntheses of (+)-proto-Quercitol and (−)-gala-Quercitol Starting from the Naturally Abundant (−)-Shikimic Acid
title_sort efficient and highly stereoselective syntheses of (+)-proto-quercitol and (−)-gala-quercitol starting from the naturally abundant (−)-shikimic acid
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7003206/
https://www.ncbi.nlm.nih.gov/pubmed/32039317
http://dx.doi.org/10.1021/acsomega.9b02986
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