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Boc保护的4-甲基脯氨酸羧酸盐的所有四种非对映异构体的高立体选择性克级合成。

Highly stereoselective gram scale synthesis of all the four diastereoisomers of Boc-protected 4-methylproline carboxylates.

作者信息

Sun Kehuan, Tao Cheng, Long Bohua, Zeng Xiaobin, Wu Zhengzhi, Zhang Ronghua

机构信息

College of Traditional Chinese Medicine, Jinan University Guangzhou 510632 China.

The First Affiliated Hospital of Shenzhen University Shenzhen 518035 China

出版信息

RSC Adv. 2019 Oct 8;9(55):32017-32020. doi: 10.1039/c9ra06827a. eCollection 2019 Oct 7.

DOI:10.1039/c9ra06827a
PMID:35530808
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9072942/
Abstract

A general and practical synthetic process for all the four diastereoisomers of Boc-protected 4-methylproline carboxylates has been developed with essentially complete stereoselectivity on the gram scale, which represents the most diastereoselective preparation of 4-methylproline derivatives to date. This synthesis features an Evans asymmetric alkylation to elegantly establish the challenging stereochemistry of the 4-methyl group, providing valuable insights for the diastereoselective preparation of 4-substituted prolines.

摘要

已开发出一种通用且实用的合成方法，可用于制备Boc保护的4-甲基脯氨酸羧酸盐的所有四种非对映异构体，在克级规模上具有基本完全的立体选择性，这是迄今为止4-甲基脯氨酸衍生物最具非对映选择性的制备方法。该合成方法的特点是采用埃文斯不对称烷基化反应，巧妙地构建了具有挑战性的4-甲基立体化学结构，为4-取代脯氨酸的非对映选择性制备提供了有价值的见解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/f51fb4ed7543/c9ra06827a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/8e65b0c511f9/c9ra06827a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/9e6b2be533d2/c9ra06827a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/0b41b1112016/c9ra06827a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/99ed6fc558e2/c9ra06827a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/953c43fbbacb/c9ra06827a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/f51fb4ed7543/c9ra06827a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/8e65b0c511f9/c9ra06827a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/9e6b2be533d2/c9ra06827a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/0b41b1112016/c9ra06827a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/99ed6fc558e2/c9ra06827a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/953c43fbbacb/c9ra06827a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9f2/9072942/f51fb4ed7543/c9ra06827a-s5.jpg

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1
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J Med Chem. 2016 Dec 8;59(23):10781-10787. doi: 10.1021/acs.jmedchem.6b01023. Epub 2016 Nov 16.
3
Nazumazoles A-C, Cyclic Pentapeptides Dimerized through a Disulfide Bond from the Marine Sponge Theonella swinhoei.
Org Lett. 2020 Jul 17;22(14):5396-5400. doi: 10.1021/acs.orglett.0c01718. Epub 2020 Jun 25.
Nazumazoles A-C，来自海绵 Theonella swinhoei 的环五肽二聚体通过二硫键形成的环状五肽。
Org Lett. 2015 Jun 5;17(11):2646-8. doi: 10.1021/acs.orglett.5b01020. Epub 2015 May 11.
4
A Lanthanide(III) Triflate Mediated Macrolactonization/Solid-Phase Synthesis Approach for Depsipeptide Synthesis.镧系元素（III）三氟甲磺酸介导的大环内酯化/固相合成方法用于去肽合成。
Org Lett. 2015 May 1;17(9):2182-5. doi: 10.1021/acs.orglett.5b00781. Epub 2015 Apr 13.
5
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J Org Chem. 2014 Oct 17;79(20):9778-91. doi: 10.1021/jo5019798. Epub 2014 Sep 29.
6
Total synthesis and stereochemical reassignment of bisebromoamide.双溴酰胺的全合成和立体化学重定义。
Org Lett. 2010 Jul 2;12(13):3018-21. doi: 10.1021/ol101021v.
7
Total synthesis of potential antitumor agent, (-)-dictyostatin.潜在抗肿瘤药物（-）-网抑素的全合成
Org Lett. 2007 Jan 4;9(1):157-60. doi: 10.1021/ol062737k.
8
Total synthesis of cyclic tetrapeptide FR235222, a potent immunosuppressant that inhibits mammalian histone deacetylases.环状四肽FR235222的全合成，一种抑制哺乳动物组蛋白脱乙酰酶的强效免疫抑制剂。
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9
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10
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