A Facile, Six-Step Process for the Synthesis of (3S,5S)-3-Isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydrofuran-2-yl)-2-oxopyrrolidine-1-carboxylic Acid tert-Butyl

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• 作者：Xianhua Pan ; Siyao Xu ; Rui Huang ; Wansheng Yu ; Feng Liu
• 刊名：Organic Process Research & Development
• 出版年：2015
• 出版时间：June 19, 2015
• 年：2015
• 卷：19
• 期：6
• 页码：611-617
• 全文大小：435K
• ISSN：1520-586X

文摘

A facile, six-step process for the synthesis of (3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydro- furan-2-yl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester from (S)-4-benzyloxazolidin-2-one 2 in an overall 50% yield is reported. The key transformations include: a highly efficient diastereoselective epoxidation, Lewis acid-catalyzed ring-opening with bromide, an S_N2 reaction using NaN₃, and a tandem reduction鈥揷yclization reaction.