The natural products (-)-dihydromenisdaurilide, (-)-3, and (+)-dihydroaquilegiolide, (+)-4, were isolated in 1993, but synthetic reports related to these compounds are quite scarce. Only a synthesis of both natural isomers in enantioenriched form and a synthesis in enantiopure form of unnatural 3 and natural 4 have been reported. Starting from an enantiopure monoketal of p-benzoquinone, we have investigated several synthetic approaches to both lactones in enantiomerically pure form, but each of them resulted in racemization. Finally, partial hydrogenation of (+)- and (-)-menisdaurilide allowed the preparation of (+)- and (-)-dihydromenisdaurilide, respectively, and a Mitsunobu reaction applied to 3 afforded (+)- and (-)-dihydroaquilegiolide. ©ARKAT USA, Inc.
|Publication status||Published - 1 Jan 2007|
- Mitsunobu reaction
- p-benzoquinone monoketals