期刊
PURE AND APPLIED CHEMISTRY
卷 81, 期 2, 页码 217-226出版社
INT UNION PURE APPLIED CHEMISTRY
DOI: 10.1351/PAC-CON-08-07-14
关键词
alkaloids; Conia-ene reaction; neooxazolomycin; salinosporamide A; total synthesis
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.
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