通过对映选择性分子内烯烃碳胺化反应全合成(S)-(+)-娃儿藤碱
Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination.
作者信息
Zeng Wei, Chemler Sherry R
机构信息
Department of Chemistry, The University at Buffalo, The State University of New York, Buffalo, New York 14260, USA.
出版信息
J Org Chem. 2008 Aug 1;73(15):6045-7. doi: 10.1021/jo801024h. Epub 2008 Jun 28.
Abstract
The enantioselective synthesis of (S)-(+)-tylophorine, a potent cancer cell growth inhibitor, has been accomplished in eight steps from commercially available 3,4-dimethoxybenzyl alcohol. A copper (II)-catalyzed enantioselective intramolecular alkene carboamination was employed as the key step to construct the chiral indolizidine ring.
摘要
强效癌细胞生长抑制剂（S）-（+）- tylophorine已从市售的3,4-二甲氧基苄醇经八步反应实现对映选择性合成。采用铜（II）催化的对映选择性分子内烯烃碳胺化反应作为构建手性中氮茚环的关键步骤。
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本文引用的文献
1
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Org Lett. 2007 Dec 20;9(26):5477-80. doi: 10.1021/ol702401w. Epub 2007 Nov 29.
2
Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes.
J Am Chem Soc. 2007 Oct 31;129(43):12948-9. doi: 10.1021/ja0762240. Epub 2007 Oct 5.
3
Structure-activity studies of phenanthroindolizidine alkaloids as potential antitumor agents.
Bioorg Med Chem Lett. 2007 Aug 1;17(15):4338-42. doi: 10.1016/j.bmcl.2007.05.021. Epub 2007 May 16.
4
Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism.
J Org Chem. 2007 May 11;72(10):3896-905. doi: 10.1021/jo070321u. Epub 2007 Apr 12.
5
Couplings of benzylic halides mediated by titanocene chloride: synthesis of bibenzyl derivatives.
J Org Chem. 2007 Mar 16;72(6):2251-4. doi: 10.1021/jo062492p. Epub 2007 Feb 20.
6
Synthesis and structure-activity studies of antofine analogues as potential anticancer agents.
Bioorg Med Chem Lett. 2007 Jan 1;17(1):97-100. doi: 10.1016/j.bmcl.2006.09.080. Epub 2006 Sep 30.
7
Inhibition of cell growth and nuclear factor-kappaB activity in pancreatic cancer cell lines by a tylophorine analogue, DCB-3503.
Mol Cancer Ther. 2006 Oct;5(10):2484-93. doi: 10.1158/1535-7163.MCT-06-0146.
8
Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C.
Chemistry. 2006 Sep 25;12(28):7398-410. doi: 10.1002/chem.200600592.
9
Antitumor agents 251: synthesis, cytotoxic evaluation, and structure-activity relationship studies of phenanthrene-based tylophorine derivatives (PBTs) as a new class of antitumor agents.
Bioorg Med Chem. 2006 Oct 1;14(19):6560-9. doi: 10.1016/j.bmc.2006.06.009. Epub 2006 Jun 30.
10
The interaction between tylophorine B and TMV RNA.
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