The Synthesis of Some Stereoisomerides of Santonin

Abe, Yasuo; Harurawa, Tadatsugu; Ishikawa, Hisashi; Miki, Takuichi; Sumi, Masao; Toga, Tadashi

doi:10.2183/pjab1945.28.425

Cited by 9 publications

(2 citation statements)

References 5 publications

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“…Disubstituted malonic acids 24b , 24d , 24g , and 24i were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

“…The resulting mixture was warmed to room temperature and stirred for 15 min. (Z)-1-Bromohex-3-ene 52 (30) was then added, and the reaction was further refluxed overnight. The reaction was monitored by TLC, and upon completion, the mixture was quenched with water (15 mL), the two layers were separated, and the aqueous phase was extracted with Et 2 O (3 × 20 mL).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone

Dewez

et al. 2018

J. Org. Chem.

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“…Disubstituted malonic acids 24b , 24d , 24g , and 24i were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone

Dewez

et al. 2018

J. Org. Chem.

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TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

Bergmann¹,

Ginsburg

Pappo

2011

Organic Reactions

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The Michael condensation in its original scope is the addition of an addend or donor containing an alpha‐hydrogen atom in the system OCCH to a carbon‐carbon double bond that forms part of a conjugated system of the general formula CCCO in an acceptor. The condensation takes place under the influence of alkaline reagents, typically alkali metal alkoxides. The range of addends is very broad. Typical acceptors are alpha, beta‐unsaturated aldehydes, keotnes, and acid derivatives. As an extension of the original scope, the Michael condensation has come to be understood to include addends and acceptors activated by groups other than carbonyl and carboxalkoxy. The wider scope is encompassed in this survey.

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Experiments on the synthesis of santonin. III. The preparation and bromination‐dehydrobromination of ethyl α‐(2:3:4:5:6:7:8: 10‐octahydro‐1: 10‐dimethyl‐2‐oxo‐7‐naphthyl)propionate

Gunstone

Tulloch

1954

J. Appl. Chem.

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Mukherjee'sl preparation of ethyl a-(4-methyl-3-oxocyclohexyl)propionate has been improved.Condensed with I-diethylaminopentan-3-one this affords ethyl a-(2 : 3 : 4 : 5 : 6 : 7 : 8 : 10octahydro-1 : lO-dirnethyl-2-oxo-7-naphthyl)propionate, the bromination4ehydrobromination of which has k e n studied. I-Chloro-and I-diethylamino-pent-I-en-3-one are described for the first time. Attempts t o condense these compounds with 2-methylcyclohexanone and with ethyl a-(4-methyl-3-oxocyclohexyl)propionate were unsuccessful.

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The Synthesis of Some Stereoisomerides of Santonin

Cited by 9 publications

References 5 publications

Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone

Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone

TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

Experiments on the synthesis of santonin. III. The preparation and bromination‐dehydrobromination of ethyl α‐(2:3:4:5:6:7:8: 10‐octahydro‐1: 10‐dimethyl‐2‐oxo‐7‐naphthyl)propionate

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