Indium-catalyzed Conia-ene reaction for alkaloid synthesis
Indium-catalyzed Conia-ene reaction for alkaloid synthesis
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DOI：
10.1351/pac-con-08-07-14
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发表时间：
2009-01
影响因子：
1.8
通讯作者：
S. Hatakeyama
中科院分区：
文献类型：
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作者：
S. Hatakeyama
摘要In(OTf)3催化氮系和氧系乙二烯二酸酯的环化反应可得到各种5 - 7元杂环，产率中等至优异，且对手性和非末端炔无外消旋反应，e选择性完全。通过合成(-)-salinosporamide A（一种高效的20S蛋白酶体抑制剂）和(+)-neooxazolomycin（一种恶唑霉素家族的抗生素），证明了这种合成的实用性。
Abstract In(OTf)3-catalyzed cyclization of nitrogen- and oxygen-tethered acetylenic malonic esters provides various five- to seven-membered heterocycles in moderate to excellent yield, and the reaction proceeds with no racemization and complete E-selectivity in the case of chiral and nonterminal alkynes. The synthetic utility is demonstrated by the synthesis of (-)-salinosporamide A, a highly potent 20S proteasome inhibitor, and (+)-neooxazolomycin, a member of the oxazolomycin family of antibiotics.