Enantioselective access to (−)-indolizidines 167B, 209D, 239AB, 195B and (−)-monomorine from a common chiral synthon

An enantioselective access to (−)-indolizidine alkaloids 167B, 209D, 239AB, 195B and (−)-monomorine from a new chiral synthon is described. The use of (S)-3-(Cbz-amino)-4-(tert-butyldimethylsilyloxy)butanal, obtained from l-aspartic acid, has provided efficient access of the indolizidine frame work...

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Bibliographic Details
Published in:Tetrahedron 2012-01, Vol.68 (1), p.145-151
Main Authors: Reddy, Chada Raji, Latha, Bellamkonda, Rao, Nagavaram Narsimha
Format: Article
Language:English
Subjects:
Alkaloids
Chemistry
Chiral synthon
Exact sciences and technology
Frames
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Horner–Wadsworth–Emmonsreaction
Indolizidine alkaloid
Organic chemistry
Preparations and properties
Reductive cyclization
Tetrahedrons
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Summary:An enantioselective access to (−)-indolizidine alkaloids 167B, 209D, 239AB, 195B and (−)-monomorine from a new chiral synthon is described. The use of (S)-3-(Cbz-amino)-4-(tert-butyldimethylsilyloxy)butanal, obtained from l-aspartic acid, has provided efficient access of the indolizidine frame work through a Horner–Wadsworth–Emmons reaction and reductive cyclization as the key steps. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.10.076