Abstract
3-Oxo-4-aza-5-pregnene-20E-oxime was synthesised from the starting material progesterone through oxidative ring cleavage, amination ring closure and oximation. The configuration of the oxime was determined from the 2D-NOESY spectrum. A series of oxime ester derivatives were obtained through the acylation of the oxime, their structures were confirmed by ESI-MS, 1H NMR, 13C NMR and HRMS.
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