- Total Synthesis of Violaceoid A and (-)- and (+)-Violaceoid B
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The first total synthesis of violaceoid A, a cytotoxic agent, and the asymmetric total synthesis of (-)- and (+)-violaceoid B are reported. The precursor was accessed by desymmetrization of a substituted quinol moiety, and the racemic secondary alcohol wa
- Murata, Takatsugu,Kuboki, Teppei,Ishikawa, Ryo,Saito, Takahiro,Taguchi, Shotaro,Takeuchi, Kazuma,Hatano, Emiko,Shimonaka, Motoyuki,Shiina, Isamu
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p. 2364 - 2370
(2018/11/23)
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- First oxidative cyclization of 1,3-bis(trimethylsilyloxy)buta-1,3-dienes
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The first oxidative cyclizations of 1,3-bis(trimethylsilyloxy)-buta-1,3-dienes, electroneutral 1,3-dicarbonyl dianion synthons, result in regioselective formation of functionalized 1,4-dihydroquinones.
- Langer,Kohler
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p. 1653 - 1654
(2007/10/03)
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- CYCLOADDITION OF 1,4-BIS-TRIMETHYLSILOXY-1,3-CYCLOHEXADIENE
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The cycloaddition reactions of 1,4-bis-trimethylsiloxy-1,3-cyclohexadiene with maleic anhydride, dimethyl acetylenedicarboxylate, diethyl fumarate and methyl acrylate have been studied.The moderate to good yields obtained in these reactions indicate that this diene will be useful in the synthesis of 1,4-oxygenated bicyclooctanes.
- Venkatasubramanian, N.,Lavala, Dakollie,Balakrishnan, P.,Polk, Malcolm,Banks, Harold D.
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p. 423 - 431
(2007/10/02)
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- Diels-Alder Syntheses with 1,4-Di-tert-butoxy-1,3-butadiene
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The title compound (DTBU) enters into cycloadditions with fumaronitrile, tetracyanoethene, maleic anhydride, diethyl azodicarboxylate, 1,2-dibenzoylethene, dimethyl acetylenedicarboxylate, p-benzoquinone, 2-carbomethoxybenzoquinone, 2-methylbenzoquinone, 1,4-naphthoquinone, 2-methyl-1,4-naphthoquinone, and 5-hydroxy-1,4-naphthoquinone.When prepared the DTBU isomers are present in the ratio E,Z:Z,Z:E,E = 45:45:10.Of these, Z,Z-DTBU appears to be unreactive.In several cases where multible Diels-Alder products were possible, two related to E,Z- or E,E-DTBU were obtained.A connection between 1H NMR data (δ and J) and stereochemical configuration and conformation was elaborated for adducts of DTBU with p-benzoquinones or maleic anhydride.
- Hiranuma, Hidetoshi,Miller, Sidney I.
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p. 3096 - 3102
(2007/10/02)
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- CHEMISTRY OF 2,5-BIS(TRIMETHYLSILOXY)FURANS. I: PREPARATION AND DIELS-ALDER REACTIONS
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A number of substituted 2,5-bis(trimethylsiloxy)furans were prepared from the corresponding succinic anhydrides, and were found to be reactive dienes from the Diels-Alder reaction with electron-withdrawing dienophiles, giving p-quinones and hydroquinones.
- Brownbridge, Peter,Chan, Tak-Hang
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p. 3423 - 3426
(2007/10/02)
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