Synthesis of (−)-dihydropinidine, (2 S,6 R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid

The use of a β-amino aldehyde derived from l-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (−)-dihydropinidine·HCl, (2 S,6 R)-isosolenopsin·HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2011-11, Vol.22 (20), p.1849-1854
Main Authors: Reddy, Chada Raji, Latha, Bellamkonda
Format: Article
Language:English
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Summary:The use of a β-amino aldehyde derived from l-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (−)-dihydropinidine·HCl, (2 S,6 R)-isosolenopsin·HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2011.11.006