Organic Process Research and Development p. 611 - 617 (2015)
Update date:2022-08-16
Topics:
Pan, Xianhua
Xu, Siyao
Huang, Rui
Yu, Wansheng
Liu, Feng
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 SN2 reaction using NaN3, and a tandem reduction-cyclization reaction.
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