期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 127, 期 32, 页码 11505-11515出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja0518880
关键词
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The total synthesis of spirotryprostatin B, a cytostatic spiro[pyrrolidine-3,3'-oxindole] alkaloid, is described. The key step of the synthetic approach consists of the application of the MgI2-mediated ring-expansion reaction of a spiro[cyclopropane-1,3'-oxindole] with an aldimine, leading to rapid assembly of the spirotryprostatin core. The route documents the installation of the prenyl side chain by Julia-Kocienski olefination of a key aldehyde precursor, a transformation that ultimately allows for facile synthesis of analogues and facilitates structure-activity relationships studies.
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