Efficient and stereoselective synthesis of bicyclo[3.2.1]octan-8-ones: synthesis and palladium-catalyzed isomerization of functionalized 2-vinyl-2,3,3a,4,5,6-hexahydro-2,3-benzofurans |
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Authors: | Langer Peter Holtz Edith Saleh Nehad N R |
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Institution: | Institut für Organische Chemie der Georg-August-Universit?t G?ttingen Tammannstrasse 2, 37077 G?ttingen, Germany. planger@uni-goettingen.de |
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Abstract: | A new C,O-cyclodialkylation of dilithiated cyclic beta-keto esters and beta-keto sulfones with 1,4-dibromo-2-butene is reported which results in regio- and diastereoselective formation of 2-vinyl-2,3,3a,4,5,6-hexahydro-2,3-benzofurans. The products could be efficiently transformed into functionalized bicyclo3.2.1]octan-8-ones by a palladium-catalyzed rearrangement reaction. In case of sulfone derivatives, this rearrangement proceeds with high stereospecifity to give exclusively the endo-configured diastereomers. The bicyclo3.2.1]octane skeleton is present in a large number of pharmacologically important natural products. |
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