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The synthesis of 1-benzyldimethylsilyl-4-phenylthio-1,3-butadiene: A new diene-regenerable diels-alder synthon

✍ Scribed by J.J. Pegram; C.B. Anderson

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 134 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)82437-5

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✦ Synopsis

1-Benzyldimethylsilyl-4-phenylthio-1,3-butadiene (L), prepared by hydrosilation of propargyl alcohol, oxidation and followed by Wittig-Horner reaction, underwent Diels-Alder reaction with methyl methacrylate. The adduct after oxidation to the sulfone when treated with fluoride gave 5-carbomethoxy-5-methyl-1,3-cyclohexadiene. Many natural products such as occindentalo11v3 , damascenone2 and the germacranolided contain or might be derived from the 1,3-cyclohexadiene functionality. Therefore it would be useful to devise a 1,3-butadiene which after an initial 4+2 cycloaddition would give an adduct that could be readily converted to a 1,3-cyclohexadiene.4 1-Benzyldimethylsilyl-4-phenylthio-1,3-butadiene (A) was prepared in three steps: hydrosilation of propargyl alcohol, oxidation to the silylpropargaldehyde and Wittig-Horner reaction

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