A new approach to the synthesis of Prelog-Djerassi Lactonic acid (1) is reported. A key step in this synthesis involves an lreland-Claisen rearrangement/silicon-mediated fragmentation sequence to provide the carbon framework in (1).
A convenient synthesis of the (±)-prelog-djerassi lactone from cyclopentanone
✍ Scribed by Christiane Santelli-Rouvier; Sophie Lefrère; Maurice Santelli
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 259 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
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 'a
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