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A Concise Synthesis of (2 R ,3 R )‐ and (2 R ,3 S )‐3‐Hydroxypipecolic Acids, and Total Synthesis of (–)‐Deoxoprosopinine and (+)‐2‐ epi ‐Deoxoprosopinine from D ‐Glycals
Author(s) -
Mallick Asadulla,
Kumari Nitee,
Roy Rashmi,
Palanivel Ashokkumar,
Vankar Yashwant D.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402603
Subject(s) - chemistry , total synthesis , intramolecular force , azide , stereochemistry , grignard reaction , formal synthesis , organic chemistry , reagent
Short and efficient formal syntheses of (2 R ,3 R )‐ and (2 R ,3 S )‐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.