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交替酸的全合成及相关研究。

Alternaric acid: formal synthesis and related studies.

机构信息

Caudill Laboratories, Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.

出版信息

Beilstein J Org Chem. 2013;9:166-72. doi: 10.3762/bjoc.9.19. Epub 2013 Jan 24.

DOI:10.3762/bjoc.9.19
PMID:23399952
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3566800/
Abstract

A silyl glyoxylate three-component-coupling methodology has been exploited to achieve a formal synthesis, an analogue to an intermediate in a distinct formal synthetic route, and a third (unique) approach to the natural product alternaric acid. Highlighted in this study is the versatility of silyl glyoxylates to engage a variety of nucleophile and electrophile pairs to provide wide latitude in the approach to complex molecule synthesis.

摘要

利用硅基乙二醛三组分偶联方法实现了一种形式合成、独特形式合成途径中的一个中间体的类似物以及天然产物交替酸的第三种(独特的)方法。本研究的重点是硅基乙二醛的多功能性,它可以与各种亲核试剂和亲电试剂对结合,从而为复杂分子合成提供广泛的方法选择。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/a68ba996204a/Beilstein_J_Org_Chem-09-166-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/3e1de5713cda/Beilstein_J_Org_Chem-09-166-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/84a16f56b23e/Beilstein_J_Org_Chem-09-166-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/dbfb73efe39a/Beilstein_J_Org_Chem-09-166-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/c134e8fb8b1e/Beilstein_J_Org_Chem-09-166-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/91521476c322/Beilstein_J_Org_Chem-09-166-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/8afe57639c1d/Beilstein_J_Org_Chem-09-166-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/ceb076f90c89/Beilstein_J_Org_Chem-09-166-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/a68ba996204a/Beilstein_J_Org_Chem-09-166-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/3e1de5713cda/Beilstein_J_Org_Chem-09-166-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/84a16f56b23e/Beilstein_J_Org_Chem-09-166-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/dbfb73efe39a/Beilstein_J_Org_Chem-09-166-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/c134e8fb8b1e/Beilstein_J_Org_Chem-09-166-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/91521476c322/Beilstein_J_Org_Chem-09-166-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/8afe57639c1d/Beilstein_J_Org_Chem-09-166-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/ceb076f90c89/Beilstein_J_Org_Chem-09-166-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f88b/3566800/a68ba996204a/Beilstein_J_Org_Chem-09-166-g009.jpg

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J Org Chem. 2012 Dec 7;77(23):10789-803. doi: 10.1021/jo302142v. Epub 2012 Nov 16.
2
Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.构建分子复杂性和多样性:生物和医学重要性天然产物的全合成。
Chem Soc Rev. 2012 Aug 7;41(15):5185-238. doi: 10.1039/c2cs35116a. Epub 2012 Jun 28.
3
Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.
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Angew Chem Int Ed Engl. 2014 Jan 3;53(1):255-9. doi: 10.1002/anie.201306873. Epub 2013 Nov 12.
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4
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5
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6
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J Am Chem Soc. 2010 Dec 15;132(49):17393-5. doi: 10.1021/ja108848d. Epub 2010 Nov 18.
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