Total synthesis of quebrachamine through macrolactamization

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题名:	Total synthesis of quebrachamine through macrolactamization
作者:	侯敦仁;Hsu, Shih-Wen;Cheng, Hsiu-Yi;Huang, An-Chi;Ho, Tse-Lok;Hou, Duen-Ren
贡献者:	理學院化學學系
关键词:	Alkaloids;Hydrogenation;Lactamization;Natural products;Total synthesis
日期:	2014-01-01
上传时间:	2026-04-21 14:22:31 (UTC+8)
出版者:	Wiley-VCH Verlag;Weinheim: WILEY-VCH Verlag
摘要:	摘要： AbstractThe total synthesis of quebrachamine was achieved through the macrolactamization of cis‐2‐alkenylated indole 17, which was prepared by a Sonogashira reaction between indole 5b and piperidine 11 followed by cis‐hydrogenation. We found that stoichiometric copper(I) iodide limited the undesired Glaser‐type homocoupling of alkyne 11 that would otherwise take place during the Sonogashira coupling. This direct approach allowed the total synthesis in ten linear steps starting from commercially available chemicals. Conditions for the reduction of lactam 19 by lithium aluminiumhydride were adjustable, so that either (±)‐quebrachamine or the analogue (±)‐kopsiyunnanine D was prepared. 其他題名： Eur. J. Org. Chem 出版者： Weinheim: WILEY-VCH Verlag 出版日期： 2014-05 出處： European Journal of Organic Chemistry, 2014-05, Vol.2014 (15), p.3109-3115 資源來源： Wiley Online Library - AutoHoldings Journals 版權： Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 版權： Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 識別號： ISSN: 1434-193X 識別號： EISSN: 1099-0690 識別號： DOI: 10.1002/ejoc.201400064
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