Synthetic application of the diels-alder adduct of β-trans-ocimene and maleic anhydride—II: An approach towards the synthesis of valerenic acid

✍ Scribed by K.T. Joseph; G.S. Krishna Rao

• Publisher: Elsevier Science
• Year: 1967
• Tongue: French
• Weight: 414 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)83377-9

✦ Synopsis

Abstnw

-By a series of reactions the Diels-Alder adduct N of maleic anhydride and &trans-Ckiine gave l-hydroxy-l,4-dimethyl-7-hydroxymcthybctahydroindane (XII). Its further synthetic elaboration furnished 1,4-dimethyl-7-(2-ethoxycarbonyl-l-propenyl)-A*-octahydroindane of the valerenic acid skeleton. VALERENIC ACID,~~ valerenolic acid2*4*s and valerena13*6*7 are interesting sesquiterpenes, the structures of which have been well established as I,' II6 and III.' These naturally occurring compounds are also of interest because of their novel sesquiterpene skeleton, valerenane which is believed to be biogenetically related to a guainolide4 or a-gujunene' precursors. $Q $f" $J 1 II 111 1