- THE CONFIGURATION OF THE SESQUITERPENOID 4-HYDROXY-MYOPORONE (ATHANAGRANDIONE)
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The conversion of eremoacetal to (-)-1-(furan-3-yl)-4-hydroxy-4,8-dimethylnonane-1,6-dione establishes the configuration of (-)-4-hydroxymyoporone (athanagrandione) as R.Key words: Ipomoea batatas; Convolvulaceae; FUsarium solani; Athanasia grandiceps; sweet potato; sesquiterpenoid; configuration; 4-hydroxymyoporone; athanagrandione; eremoacetal.
- Dimitriadis, Eugene,Massy-Westropp, Ralph A.
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- Synthesis of 3-Acylfurans Using 3-(Phenylthio)propanal Dimethyl Acetal as a New Synthon. Syntheses of Ipomeanine and Isoegomaketone
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It was found that 3-(phenylthio)propanal dimethyl acetal is a very useful starting material for the preparation of 3-acylfuranoterpenes.Syntheses of two naturally-occurring furans, isoegomaketone and ipomeanine were described.
- Watanabe, Eiji,Imai, Naohiro,Inomata, Katsuhiko,Kinoshita, Hideki,Kotake, Hiroshi
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- Palladium-Catalyzed Reductive Coupling of Acid Chlorides with β-Stannyl Enones: Synthesis of 1,4-Diketones and Mechanistic Aspects
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The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or β-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl intermediate.The double bond conjugated with a single carbonyl group was not significantly reduced.The generality of the method is illustrated by two syntheses of the 1,4-diketone ipomeanine.By performing the reaction at lower temperatures, α,β-unsaturated 1,4-diketones can also be prepared.The reduction of the intermediate α,β-unsaturated 1,4-diketones probably proceeds by insertion of a palladium hydride, formed in situ by reaction of a Pd(II) complex with Bu3SnCl, followed by hydrolysis of the intermediate palladium enolate.
- Echavarren, Antonio M.,Perez, Marta,Castano, Ana M.,Cuerva, Juan M.
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p. 4179 - 4185
(2007/10/02)
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- Synthesis of 1,4-Diketones by Palladium-Catalyzed Reductive Coupling of Acid Chlorides with (E)-1,2-Bis(tri-n-butylstannyl)ethene or β-Stannyl Enones
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The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or β-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl derivative by a palladium hydride derived from n-Bu3SnCl.
- Perez, Marta,Castano, Ana M.,Echavarren, Antonio M.
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p. 5047 - 5049
(2007/10/02)
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