Synthesis of spiro[5.4]decenones and their transformation into bicyclo[4.4]deca-1,4-dien-3-ones by domino "elimination- double-Wagner-Meerwein-rearrangement" reactions |
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| Authors: | Bose Gopal Ullah Ehsan Langer Peter |
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| Institution: | Institut für Chemie und Biochemie der Ernst-Moritz-Arndt Universit?t Greifswald, Soldmannstrasse 16, 17487 Greifswald, Germany. |
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| Abstract: | The 3+3] cyclization of 1,3-bis-silyl enol ethers with 1,1-diacylcyclopentanes allows a convenient synthesis of spiro5.4]decenones. Treatment of these compounds with trifluoroacetic acid (TFA) afforded a great variety of bicyclo4.4.0]deca-1,4-dien-3-ones containing an angular alkyl group. This core structure occurs in a number of pharmacologically relevant natural products. |
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| Keywords: | cyclization domino reactions rearrangement silyl enol ethers spiro compounds |
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