A concise and convergent route to 5,8-disubstituted indolizidine and 1,4-disubstituted quinolizidine ring cores by diastereoselective aza-Diels-Alder reaction |
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Authors: | Barluenga José Mateos Carlos Aznar Fernando Valdés Carlos |
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Institution: | Instituto Universitario de Química Organometálica Enrique Moles, Unidad asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Spain. barluenga@sauron.quimica.uniovi.es |
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Abstract: | reaction: see text] A short and convergent synthesis of 5,8-disubstituted indolizidine and 1,4-quinolizidine scaffolds is described. The key steps of the synthetic pathway are the aza-Diels-Alder reaction of a 2-aminodiene with an N-allyl or N-homoallylaldimine and a ring-closing metathesis. The bicyclic alkaloid analogues are obtained with total diastereoselectivity and through a common pathway. |
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