Synthesis of 6-(1-hydroxyethyl)-1,1-dimethyl-1-carba-2-penem derivatives via dieckmann-type cyclization |
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| Authors: | Masayuki Shibuya Masahiko Kuretani Seiju Kubota |
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| Institution: | Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi 1, Tokushima 770, Japan |
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| Abstract: | Three diaastereomers of 4 - (1,1 -dimethyl - 2 - propenyl) - 3 - hydroxyethyl - 2 -azetidinones 2, 3, and 11 were obtained by the reaction of acetaldehyde with the enolate of the silyl azetidinone 5 and dilithiated intermediate 10: The trans isomers 2 and 3 were converted into 6 - (1 - hydroxyethyl) - 1,1 - dimethyl - 1 - carba - 2 - penems 19 and 20via a Dieckmann-type cyclization. |
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