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Enantioselective synthesis of R-(−)-ligularenolide and the progesterone receptor ligand R-(−)-PF1092C starting from S-(+)-carvone

✍ Scribed by Louis H.D. Jenniskens; Aede de Groot

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
370 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

A new enantioselective synthesis of eremophilane sesquiterpenes was developed starting from S-(+)-carvone 3, using a conjugate addition-annelation sequence. The synthesis of R-(-)-Iigularenolide 1 was accomplished in a staightforward manner with the annelation of the lactone as the last step. For the synthesis of the progesterone receptor ligand R-(-)-PF1092C 2 a different strategy was followed in which first the lactone was annelated. The coneommitant isomerization of the double bond of the isopropenyl group into the conjugate position then offered an alternative way to remove the side chain and simultanuously provide for an ideal functionality for the introduction of the cis 15-diol function at the C2,C3 position.

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Enantioselective synthesis of cadinanes
Enantioselective synthesis of cadinanes starting from R-(−)- or S-(+)-carvone
✍ Alexander V. Baranovsky; Ben J.M. Jansen; Tommi M. Meulemans; Aede de Groot 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 659 KB

A new enantioselective synthesis of cadinanes, using the Mukaiyama-Michael reaction, was developed starting from R-(-)-or S-(+)-carvone. This approach gives an easy and direct access to the cadinane skeleton and the scope proved to be complementary to a formylation-annelation sequence. The applicabi