A Concise Synthesis of (2R,3R)- and (2R,3S)-3-Hydroxypipecolic Acids, and Total Synthesis of (–)-Deoxoprosopinine and (+)-2-epi-Deoxoprosopinine from D-Glycals

摘要

Short and efficient formal syntheses of (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids, and total syntheses of (–)-deoxoprosopinine and (+)-2-epi-deoxoprosopinine have been achieved starting from D-glycals. The key steps involved in these syntheses were Ferrier rearrangement, azide reduction, intramolecular cyclization, and Grignard reaction.