Synthesis of Chiral 1,3-Dienes through Ring-Closing Metathesis of Enantioenriched Enynes: Potential Precursors of Morphane Analogs



Document title: Synthesis of Chiral 1,3-Dienes through Ring-Closing Metathesis of Enantioenriched Enynes: Potential Precursors of Morphane Analogs
Journal: Anais da Academia Brasileira de Ciencias
Database: PERIÓDICA
System number: 000419767
ISSN: 0001-3765
Authors: 1
1
1
1
Institutions: 1Universidad de Alicante, Facultad de Ciencias, Alicante. España
Year:
Season: May
Volumen: 90
Number: 1
Pages: 1059-1072
Country: Brasil
Language: Inglés
Document type: Artículo
Approach: Experimental, aplicado
English abstract A simple methodology for the synthesis of enynes by indium mediated diastereoselective allylation of aromatic N-tert-butanesulfinylimines bearing alkenyl groups at ortho-position with allyl bromide has been developed. The addition of the allyl indium intermediate to the chiral imine took place with excellent diastereoselectivity. Ruthenium-catalyzed ring-closing metathesis of the resulting enynes provided the expected cyclic 1,3-dienes in good to moderate yields. These chiral dienes are potential precursors of biologically and pharmacologically active morphane derivatives
Disciplines: Medicina,
Química
Keyword: Química farmacéutica,
Compuestos quirales,
Síntesis química,
Eninas,
Alilación,
Metátesis,
Alcaloides
Keyword: Medicinal chemistry,
Chiral compounds,
Chemical synthesis,
Enynes,
Allylation,
Metathesis,
Alkaloids
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