1964
DOI: 10.1021/ja01064a026
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Synthesis of Some Resin Acids

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Cited by 75 publications
(39 citation statements)
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“…[46] Resolution of (±)-desoxypodocarpic acid is achieved by treatment with cinchonine alkaloid 237, whereas the epimeric (±)deisopropyldehydroabietic acid is best resolved with the N-methylcinchonium hydroxide salt 360. Scheme 100.…”
Section: Carboxylic Acid Resolution: Cinchonine Saltmentioning
confidence: 99%
“…[46] Resolution of (±)-desoxypodocarpic acid is achieved by treatment with cinchonine alkaloid 237, whereas the epimeric (±)deisopropyldehydroabietic acid is best resolved with the N-methylcinchonium hydroxide salt 360. Scheme 100.…”
Section: Carboxylic Acid Resolution: Cinchonine Saltmentioning
confidence: 99%
“…[46,47] Die Anellierung mit Pyrrolidin (über ein Enamin-Intermediat) war wesentlich effizienter als andere basische Bedingungen, insbesondere fürH ydrindenonsysteme. [46,47] Die Anellierung mit Pyrrolidin (über ein Enamin-Intermediat) war wesentlich effizienter als andere basische Bedingungen, insbesondere fürH ydrindenonsysteme.…”
Section: Aldolcyclisierungunclassified
“…[46] Die Enantiomerentrennung von (AE)-Desoxypodocarpinsäure gelang durch die Umsetzung mit Cinchonin-Alkaloid 237,w ährend die epimere (AE)-Deisopropyldehydroabietinsäure (360)a mb esten als N-Methylcinchoniumhydroxid-Salz aufgetrennt wurde. [46] Die Enantiomerentrennung von (AE)-Desoxypodocarpinsäure gelang durch die Umsetzung mit Cinchonin-Alkaloid 237,w ährend die epimere (AE)-Deisopropyldehydroabietinsäure (360)a mb esten als N-Methylcinchoniumhydroxid-Salz aufgetrennt wurde.…”
Section: Enantiomerentrennung Durch Carbonsäuren:cinchoninsalzunclassified
“…As shown by the p.m.r. spectrum, this material consisted largely of one diastereomer, and, although the stereochemistry was not rigorously established, literature precedent (30) indicated that the newly alkylated center should possess the configuration shown in 13. In any event, this point was not crucial, since the next step of the synthesis involved hydrolysis and decarboxylative removal of the tertiary carbo~nethoxy moiety.…”
Section: [Traduit Par Le Journal]mentioning
confidence: 98%
“…An alternative, direct conversion of the octalone 7 into the keto ester 12 involving base-promoted condensation of the former with dimethyl carbonate was also considered. However, on the basis of literature precedent (30), it was felt that a reaction of this type would result in carbomethoxylation of 7 at C-1 as well as at the desired position (C-3). Indeed, this direction conversion was later attempted (1 lb) and the product, although claimed to be 12, was not obtained crystalline and no criterion of purity was given.…”
Section: [Traduit Par Le Journal]mentioning
confidence: 99%