Suppr超能文献

δ(13)-9-异呋喃的发散合成

A divergent synthesis of the delta(13)-9-isofurans.

作者信息

Taber Douglass F, Gu Peiming, Li Rui

机构信息

Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.

出版信息

J Org Chem. 2009 Aug 7;74(15):5516-22. doi: 10.1021/jo900767x.

DOI:10.1021/jo900767x
PMID:19572754
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2736316/
Abstract

A stereodivergent total synthesis of the Delta(13)-9-isofurans has been developed. The four core substituted tetrahydrofurans were prepared by the Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation followed by cascade cyclization. The relative configuration at C-8 was inverted by oxidation followed by immediate L-Selectride reduction. The relative configuration of the C-15 diastereomers was assigned by (S)-Binol/LAH/EtOH reduction of the corresponding enone. This synthesis of the Delta(13)-9-isofurans will provide sufficient material for further investigation of their biological activity.

摘要

已开发出一种立体发散性全合成Δ(13)-9-异呋喃的方法。通过夏普莱斯不对称环氧化和夏普莱斯不对称双羟基化反应，随后进行串联环化反应，制备了四个核心取代的四氢呋喃。通过氧化，然后立即用L-选择氢化物还原，使C-8处的相对构型发生反转。通过用(S)-联萘酚/氢化铝锂/乙醇还原相应的烯酮，确定了C-15非对映异构体的相对构型。这种Δ(13)-9-异呋喃的合成将为进一步研究其生物活性提供足够的材料。

相似文献

1
A divergent synthesis of the delta(13)-9-isofurans.
J Org Chem. 2009 Aug 7;74(15):5516-22. doi: 10.1021/jo900767x.
2
Synthesis of cis- and trans-2,5-disubstituted tetrahydrofurans by a tandem dihydroxylation-SN2 cyclization sequence.
Org Lett. 2005 Oct 27;7(22):4819-22. doi: 10.1021/ol051507n.
3
Synthesis of the enediol isofurans, endogenous oxidation products of arachidonic acid.
J Org Chem. 2006 Feb 3;71(3):926-33. doi: 10.1021/jo051889a.
4
Stereodivergent organocatalytic intramolecular Michael addition/lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans.
Chemistry. 2014 Jul 28;20(31):9762-9. doi: 10.1002/chem.201402684. Epub 2014 Jul 2.
5
Stereodivergent strategy for neurofuran synthesis via palladium-catalyzed asymmetric allylic cyclization: total synthesis of 7-epi-ST-Δ(8)-10-neurofuran.
J Org Chem. 2013 Jun 7;78(11):5556-67. doi: 10.1021/jo4004647. Epub 2013 May 14.
6
Intramolecular displacement of phenylselenone by a hydroxy group: stereoselective synthesis of 2-substituted tetrahydrofurans.
Org Lett. 2013 Aug 2;15(15):3906-9. doi: 10.1021/ol401653w. Epub 2013 Jul 19.
7
A nomenclature system for isofurans.
Prostaglandins Other Lipid Mediat. 2004 Jan;73(1-2):47-50. doi: 10.1016/j.prostaglandins.2003.11.004.
8
Total Synthesis of (-)-Alstofolinine A through a Furan Oxidation/Rearrangement and Indole Nucleophilic Cyclization Cascade.
Angew Chem Int Ed Engl. 2019 Apr 1;58(15):4988-4991. doi: 10.1002/anie.201900156. Epub 2019 Mar 6.
9
De novo asymmetric syntheses of muricatacin and its analogues via dihydroxylation of dienoates.
J Org Chem. 2006 Aug 18;71(17):6686-9. doi: 10.1021/jo061057s.
10
A practical total synthesis of (+)-spirolaxine methyl ether.
J Org Chem. 2010 Dec 3;75(23):8307-10. doi: 10.1021/jo1016647. Epub 2010 Nov 8.

本文引用的文献

1
Synthetic studies toward pectenotoxin 2. Part I. Stereocontrolled access to the C10-C22 fragment.
Org Lett. 2008 Oct 2;10(19):4179-82. doi: 10.1021/ol8015868. Epub 2008 Sep 3.
2
Beyond prostaglandins--chemistry and biology of cyclic oxygenated metabolites formed by free-radical pathways from polyunsaturated fatty acids.
Angew Chem Int Ed Engl. 2008;47(32):5894-955. doi: 10.1002/anie.200705122.
3
Synthesis of the enediol isofurans, endogenous oxidation products of arachidonic acid.
J Org Chem. 2006 Feb 3;71(3):926-33. doi: 10.1021/jo051889a.
4
A flexible enantioselective synthesis of the isofurans.
J Org Chem. 2004 Oct 15;69(21):7234-40. doi: 10.1021/jo048863o.
5
A nomenclature system for isofurans.
Prostaglandins Other Lipid Mediat. 2004 Jan;73(1-2):47-50. doi: 10.1016/j.prostaglandins.2003.11.004.
6
Total synthesis of isoprostanes: discovery and quantitation in biological systems.
Chem Phys Lipids. 2004 Mar;128(1-2):35-56. doi: 10.1016/j.chemphyslip.2003.09.011.
7
Recent advances in the stereoselective synthesis of isoprostanes and neuroprostanes.
Chem Phys Lipids. 2004 Mar;128(1-2):3-14. doi: 10.1016/j.chemphyslip.2003.10.005.
8
Treatment with a catalytic antioxidant corrects the neurobehavioral defect in ataxia-telangiectasia mice.
Free Radic Biol Med. 2004 Apr 1;36(7):938-42. doi: 10.1016/j.freeradbiomed.2004.01.003.
9
Discovery of lipid peroxidation products formed in vivo with a substituted tetrahydrofuran ring (isofurans) that are favored by increased oxygen tension.
Proc Natl Acad Sci U S A. 2002 Dec 24;99(26):16713-8. doi: 10.1073/pnas.252649099. Epub 2002 Dec 13.
10
Preparation of isoprostanes and neuroprostanes.
J Am Chem Soc. 2002 Oct 23;124(42):12424-5. doi: 10.1021/ja027451z.

文献AI研究员

20分钟写一篇综述，助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型，支持多种主流文档格式。

立即体验