Asymmetric synthesis of (-)-brevipolide H through cyclopropanation of the α,β-unsaturated ketone

Please use this identifier to cite or link to this item: https://ir.lib.ncu.edu.tw/handle/987654321/101293

Title:	Asymmetric synthesis of (-)-brevipolide H through cyclopropanation of the α,β-unsaturated ketone
Authors:	侯敦仁;Lin, Jing-Wen;Kurniawan, Yudhi Dwi;Chang, Wen-Jung;Leu, Wohn-Jenn;Chan, She-Hung;Hou, Duen-Ren
Contributors:	理學院化學學系
Keywords:	Antineoplastic Agents - chemical synthesis;Antineoplastic Agents - chemistry;Antineoplastic Agents - pharmacology;CCR5 receptor;CCR5 Receptor Antagonists - chemical synthesis;CCR5 Receptor Antagonists - chemistry;CCR5 Receptor Antagonists - pharmacology;chemical reactions;Cyclopropanes - chemical synthesis;Cyclopropanes - chemistry;Cyclopropanes - pharmacology;cytotoxicity;Humans;Hyptis - chemistry;Inhibitory Concentration 50;Ketones - chemical synthesis;Ketones - chemistry;moieties;Molecular Structure;neoplasm cells;neoplasms;organic compounds;Pyrones - chemical synthesis;Pyrones - chemistry;Pyrones - pharmacology;Stereoisomerism;sulfur
Date:	2014-10-17
Issue Date:	2026-04-21 14:29:31 (UTC+8)
Publisher:	American Chemical Society;United States: American Chemical Society
Abstract:	摘要： Brevipolides are 5,6-dihydro-γ-pyrone derivatives, first reported in 2004 as the inhibitors of the chemokine receptor CCR5 and exhibiting cytotoxicity against cancer cells. Starting from the C 2 symmetric diene-diol 2, ent-brevipolide H was synthesized for the first time in 11 steps. The anti-addition of the sulfur ylide to the α,β-unsaturated enones was developed to give the key cyclopropane moiety. The synthetic (−)-brevipolide H showed an IC50 value of 7.7 μM against PC-3 cells. 其他題名： Org. Lett 出版者： United States: American Chemical Society 出版日期： 2014-10-17 出處： Organic letters, 2014-10, Vol.16 (20), p.5328-5331 資源來源： American Chemical Society Journals 版權： Copyright © 2014 American Chemical Society 識別號： ISSN: 1523-7060 識別號： ISSN: 1523-7052 識別號： EISSN: 1523-7052 識別號： DOI: 10.1021/ol502507k 識別號： PMID: 25275479
Appears in Collections:	[Department of Chemistry] journal & Dissertation

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