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- W2896769068 abstract "The first section of this thesis describes the development of an enantioselective synthesisof terminally unsubstituted methylenecyclopropanes. The key feature of this approach is a Rh2(STBPTTL)4-mediated catalytic asymmetric cyclopropanation of unsubstituted allene to produceenantioenriched methylenecyclopropanes bearing alkyl or activated ester functionalities. Thismethod was successfully applied to the enantioselective total synthesis of cycloclavine.The second section of this thesis describes the development of an improved 12steps/5.2% overall yield racemic total synthesis of the clavine alkaloid cycloclavine. The firstenantioselective total syntheses of the unnatural enantiomer (–)-cycloclavine and the naturalenantiomer (+)-cycloclavine were also accomplished in 8 steps/7.1%(brsm) overall yield and 8steps/4% overall yield, respectively. Noteworthy features of this approach include a strainpromotedintramolecular Diels-Alder reaction followed by a highly regioselective aerobic α,β-dehydrogenation to form a key enone intermediate in >99.5:0.5 er after crystallization.Additional noteworthy features include the enone 1,2-addition of a novel TEMPO-carbamateaminomethyl carbanion and an IMDAF reaction to install the indole core. The mechanism ofthermolysis of the new TEMPOC amine protecting-group was investigated. Finally, the naturaland unnatural enantiomers were evaluated for their ability to bind to several neurotransmitterreceptors in radioligand binding assays." @default.
- W2896769068 created "2018-10-26" @default.
- W2896769068 creator A5014175197 @default.
- W2896769068 date "2018-09-27" @default.
- W2896769068 modified "2023-09-24" @default.
- W2896769068 title "ENANTIOSELECTIVE CYCLOPROPANATIONS OF ALLENES AND THEIRAPPLICATION TO THE TOTAL SYNTHESIS OF CLAVINE ALKALOIDS" @default.
- W2896769068 hasPublicationYear "2018" @default.
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