The Journal of Organic Chemistry

Convenient synthesis of jasmonoid compounds from. gamma.-(trimethylsiloxy) butyronitrile

I Matsuda, S Murata, Y Izumi

Index: Matsuda, Isamu; Murata, Shizuaki; Izumi, Yusuke Journal of Organic Chemistry, 1980 , vol. 45, # 2 p. 237 - 240

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Citation Number: 46

Abstract

1, CDioxygenated compounds 4 are constructed by the addition of a Grignard reagent to y- (trimethylailoxy) nitriles 1, 2, and 3 and subsequent hydrolysis. Oxidation of 4 with pyridinium chlorochromate or Jones reagent yields compounds 5 which are used to produce cyclopentenones 6. Methyl jasmonate and methyl dihydrojasmonate are made by the conjugate addition of silylated ketene acetal 9 to 6a and 6b, respectively, and subsequent ...

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