Stereoselective Michael Addition of Carbon-, Nitrogen-, Oxygen-, and Sulfur-Centered Nucleophiles on Enantiopure Hydroxylated 6,7-Dehydro-5-oxoindolizidine. Synthesis of Carbon- or Hetero-7-Substituted Swainsonine Analogues

Stereoselective Michael Addition of Carbon-, Nitrogen-, Oxygen-, and Sulfur-Centered Nucleophiles on Enantiopure Hydroxylated 6,7-Dehydro-5-oxoindolizidine. Synthesis of Carbon- or Hetero-7-Substituted Swainsonine Analogues

Enantiopure α,β-unsaturated δ-lactams 1 and 2 react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate additions is demonstrated through the synthesis of two new substituted indolizidines:  (7R)-7-amino-8-deoxyswainsonine...

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Veröffentlicht in:Journal of organic chemistry 2006-08, Vol.71 (17), p.6630-6633
Hauptverfasser: Tinarelli, Alessandro, Paolucci, Claudio
Format: Artikel
Sprache:eng
Schlagworte:
Carbon - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydroxylation
Indolizines - chemistry
Molecular Structure
Nitrogen - chemistry
Organic chemistry
Oxygen - chemistry
Preparations and properties
Stereoisomerism
Sulfur - chemistry
Swainsonine - analogs & derivatives
Swainsonine - chemical synthesis
Swainsonine - chemistry
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Zusammenfassung:Enantiopure α,β-unsaturated δ-lactams 1 and 2 react stereoselectively with carbon-, nitrogen-, sulfur-, and oxygen-centered nucleophiles. The synthetic potential of these conjugate additions is demonstrated through the synthesis of two new substituted indolizidines:  (7R)-7-amino-8-deoxyswainsonine 3 and (7R)-7-acetylaminoswainsonine 4.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060511p