Journal of Organic Chemistry p. 237 - 240 (1980)
Update date:2022-07-31
Topics:
Matsuda, Isamu
Murata, Shizuaki
Izumi, Yusuke
1,4-Dioxygenated compounds 4 are constructed by the addition of a Grignard reagent to γ-(trimethylsiloxy)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 protodesilylation. γ-Jasmolactone is also derived from 4a by oxidation with pyridinium dichromate in DMF followed by reduction with NaBH4 in ethanol.
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Doi:10.1139/v79-543
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(2021)Doi:10.1021/acs.orglett.5b01281
(2015)Doi:10.1055/s-2002-35221
(2002)Doi:10.1021/jm00176a021
(1980)Doi:10.1002/ejoc.201402668
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