Synthesis of (+)- and (-)-dihydromenisdaurilide and (+)- and (-)-dihydroaquilegiolide

Ramon Alibés, Mariona Cantó, Pedro De March, Marta Figueredo, Josep Font

Research output: Contribution to journalArticleResearchpeer-review

Abstract

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.
Original languageEnglish
Pages (from-to)120-131
JournalArkivoc
Volume2007
Issue number4
Publication statusPublished - 1 Jan 2007

Keywords

  • Dihydroaquilegiolide
  • Dihydromenisdaurilide
  • Mitsunobu reaction
  • p-benzoquinone monoketals

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