Concise asymmetric synthesis of (−)-halosaline and (2R,9aR)-(+)-2-hydroxy-quinolizidine by ruthenium-catalyzed ring-rearrangement metathesis |
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| Authors: | Giordano Lesma Andrea Virdis |
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| Institution: | Dipartimento di Chimica Organica e Industriale e Centro Interdisciplinare Studi biomolecolari e applicazioni Industriali (CISI), Università degli Studi di Milano, via G. Venezian 21, 20133 Milano, Italy |
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| Abstract: | A ruthenium-catalyzed ring opening-ring closing metathesis reaction serves as the key step in the stereoselective synthesis of a new enantiopure 2-substituted-4,5-dehydropiperidine skeleton, a valuable intermediate for the synthesis of piperidine alkaloids (such as (−)-halosaline) and of hydroxylated quinolizidines (such as (2R,9aR)-(+)-2-hydroxy-quinolizidine). |
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| Keywords: | Piperidine alkaloids Quinolizidine Ring rearrangement metathesis Grubbs' catalyst |
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