The fused quinuclidine-valerolactone system Synthesis and conformation of 4-alkyl or 4-aryl-6-oxa-1-azatricyclo (4.2.2.027) dodecan-5-one |
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Authors: | A Fisher E Oppenheimer S Cohen |
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Institution: | Institute for Biological Research, Ness Ziona and Sackler School of Medicine, Tel Aviv University, Israel |
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Abstract: | Michael addition of ethyl malonate, alkylmalonate and phenylacetate to 2-methylene-quinuclidin-3-one, followed by NaBH4 reduction of the 3-oxo group in the resulting adduct, then acid hydrolysis and decarboxylation (in the case of malonates) gave 6-oxa-1-azatricyclo-(4.2.2.02,7)dodecan-5-one, its 4-alkyl and 4-aryl derivatives. A minor byproduct is 2-(trans-3-hydroxyquinuclidin-2-yl)-α-alkyl-propanoic acid which is unable to undergo cyclization to δ-lactone. |
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