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 Ester, The Key Synthetic Intermediate of Aliskiren

作者：Pan Xianhua; Xu Siyao; Huang Rui; Yu Wansheng; Liu Feng^*

来源：Organic Process Research & Development, 2015, 19(6): 611-617.

DOI：10.1021/acs.oprd.5b00009

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(N)2 reaction using NaN3, and a tandem reduction-cyclization reaction.

• 出版日期2015-6
• 单位上海应用技术大学