Synthesis of (-)-deoxoprosophylline, (+)-2- epi -deoxoprosopinine, and (2 R,3 R)- and (2 R,3 S)-3-hydroxypipecolic acids from d -glycals

摘要

(Figure presented) New syntheses of (-)-deoxoprosophylline, (+)-2-epi-deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids are reported. Utilization of the chiral functionalities of Perlin aldehydes, derived from 3,4,6-tri-O-benzyl glycals, has been done along with chemoselective saturation of olefins and reductive aminations as key steps.