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Selective methodologies for the synthesis of biologically active piperidinic compounds
Author(s) -
Cossy Janine
Publication year - 2005
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.20035
Subject(s) - biological activity , combinatorial chemistry , chemistry , computational biology , biochemical engineering , biochemistry , biology , engineering , in vitro
The synthesis of optically active substituted piperidines has been achieved by using four different methodologies. The first one is an intramolecular nucleophilic displacement of activated alcohol moieties that was used to build up the piperidine ring of (−)‐prosophylline and (−)‐slaframine, and the second one is a ring‐closing metathesis of unsaturated amines which was employed in the synthesis of (+)‐sedamine and 4a,5‐dihydrostreptazoline. The third methodology is the α‐functionalization of N ‐Boc piperidines which was particularly useful in the synthesis of argatroban, and the fourth one is a ring expansion of prolinols to 3‐chloropiperidines or 3‐hydroxypiperidines which was utilized to synthesize (−)‐paroxetine, (−)‐pseudoconhydrine, the piperidine ring of (−)‐velbanamine and (+)‐zamifenacin. © 2005 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 5: 70–80; 2005: Published online in Wiley InterScience ( www.interscience.wiley.com ) DOI 10.1002/tcr.20035