First total synthesis of kipukasin A

In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra-O-acetyl-β-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2-O-isopropylidene-α-D-ribofuranose. For the first...

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Detalles Bibliográficos
Autores principales: Li, Chuang, Ding, Haixin, Ruan, Zhizhong, Zhou, Yirong, Xiao, Qiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433220/
https://www.ncbi.nlm.nih.gov/pubmed/28546843
http://dx.doi.org/10.3762/bjoc.13.86
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author Li, Chuang
Ding, Haixin
Ruan, Zhizhong
Zhou, Yirong
Xiao, Qiang
author_facet Li, Chuang
Ding, Haixin
Ruan, Zhizhong
Zhou, Yirong
Xiao, Qiang
author_sort Li, Chuang
collection PubMed
description In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra-O-acetyl-β-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2-O-isopropylidene-α-D-ribofuranose. For the first time, ortho-alkynylbenzoate was used as protecting group for the 5-hydoxy group. After subsequent Vorbrüggen glycosylation, the protecting group could be removed smoothly in the presence of 5 mol % Ph(3)PAuOTf in dichloromethane to provide kipukasin A in high yield and regioselectivity.
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spelling pubmed-54332202017-05-25 First total synthesis of kipukasin A Li, Chuang Ding, Haixin Ruan, Zhizhong Zhou, Yirong Xiao, Qiang Beilstein J Org Chem Full Research Paper In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra-O-acetyl-β-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2-O-isopropylidene-α-D-ribofuranose. For the first time, ortho-alkynylbenzoate was used as protecting group for the 5-hydoxy group. After subsequent Vorbrüggen glycosylation, the protecting group could be removed smoothly in the presence of 5 mol % Ph(3)PAuOTf in dichloromethane to provide kipukasin A in high yield and regioselectivity. Beilstein-Institut 2017-05-09 /pmc/articles/PMC5433220/ /pubmed/28546843 http://dx.doi.org/10.3762/bjoc.13.86 Text en Copyright © 2017, Li et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Li, Chuang
Ding, Haixin
Ruan, Zhizhong
Zhou, Yirong
Xiao, Qiang
First total synthesis of kipukasin A
title First total synthesis of kipukasin A
title_full First total synthesis of kipukasin A
title_fullStr First total synthesis of kipukasin A
title_full_unstemmed First total synthesis of kipukasin A
title_short First total synthesis of kipukasin A
title_sort first total synthesis of kipukasin a
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433220/
https://www.ncbi.nlm.nih.gov/pubmed/28546843
http://dx.doi.org/10.3762/bjoc.13.86
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AT ruanzhizhong firsttotalsynthesisofkipukasina
AT zhouyirong firsttotalsynthesisofkipukasina
AT xiaoqiang firsttotalsynthesisofkipukasina

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