The Grieco intermediate 2, for the synthesis of the Prelog-Djerassi lactone, was obtained from trans-pulegenic acid 3 in 6 steps in 43 9b overall yield; recycling unwanted diastereoisomer SCS\_I, increased the yield to 56 %. The Prelog-Djerassi lactone 1 is a key degradation product of the antibioti
An efficient synthesis of the Prelog-Djerassi lactone methyl ester from (-)-trans-pulegenic acid
โ Scribed by Salih Hacini; Maurice Santelli
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 403 KB
- Volume
- 46
- Category
- Article
- ISSN
- 0040-4020
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โฆ Synopsis
The (+)-Prelog-Djetassi lactone methyl ester 1 was obtained from tmns-pulegenic acid 2 in seven steps jn 22 % overall YjeJd; three more steps from an unwanted dkstereoisomergave additionnal5 %. Resume : L 'ester methylique de la Iactone de Prelog-Djemssi I a et6 obtenu en sept &apes i partir de I 'acide pulegenique 2 avec un rendement global de 22 %; le traitement en trois &apes d'un diastereoisomere non souhaite foumit 5 % supplementaire.
๐ SIMILAR VOLUMES
Thioamides 4 were transformed by two convenient routes to various functionalized enamines 7 containing different electron-withdrawing groups E which on subsequent hydrolysis gave the corresponding methyl ketone derivatives 8. Application of this methodology to obtain modified dipeptides at the carb