Please use this identifier to cite or link to this item: https://scholarbank.nus.edu.sg/handle/10635/162448
Title: ENANTIOSELECTIVE PHOSPHINE-CATALYZED ANNULATION TO CONSTRUCT SPIROOXINDOLES AND COMPLEX INDOLE ALKALOIDS THEREOF
Authors: CHAN WAI LUN
Keywords: phosphines, organocatalysis, annulations, allenes, spirooxindoles, enantioselective synthesis
Issue Date: 18-Jun-2019
Citation: CHAN WAI LUN (2019-06-18). ENANTIOSELECTIVE PHOSPHINE-CATALYZED ANNULATION TO CONSTRUCT SPIROOXINDOLES AND COMPLEX INDOLE ALKALOIDS THEREOF. ScholarBank@NUS Repository.
Abstract: The tachytelic evolution of asymmetric phosphine catalysis, over the past few decades, has forged a novel synthetic platform to access highly functionalized chiral molecular frameworks, leading an impetus to contemporary medicinal and pharmaceutical research. However, demonstrations of such methodology in target-oriented asymmetric syntheses of privileged scaffolds and bioactive natural products are still exiguous, if not elusive. This thesis is principally concerned with the strategic exploitations of underdeveloped sterically-congested substrates (e.g. isatin-derived ketimines & isoindigo-based tetrasubstituted alkenes as new 2-equivalent annulation synthons) in highly enantioselective, diastereoselective and even regioselective phosphine-catalyzed formal [3+2] spirocyclizations in general, and with the practical and creative transformations of the enantioenriched spiro-products towards the core structures of bioactive multi-substituted (5’-alkyl) 3,2’-pyrrolidinyl spirooxindoles and complex dimeric hexahydropyrroloindole alkaloids possessing vicinal quaternary stereogenic centers in particular. An unpublished work on the potential discovery of the first enantioselective phosphine-triggered intramolecular Diels–Alder reaction of bis(divinyl) ketones is also finally detailed.
URI: https://scholarbank.nus.edu.sg/handle/10635/162448
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