Journal
TETRAHEDRON
Volume 69, Issue 30, Pages 6129-6143Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.05.055
Keywords
Pyrrolidine; Piperidine; Henry; Nef; Chiral pool; 2-Substituted; Alkaloids
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Funding
- DST, New Delhi
- CSIR, New Delhi
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The paper describes the synergistic protocol developed by combinatorial Henry and Nef reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (-)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of beta-amino acids from alpha-amino acids. (C) 2013 Published by Elsevier Ltd.
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