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Total Synthesis as an Inspiration for Methodology Development: From Natural Products to Novel s-Tetrazines and the Study of Their Reactivity


Schnell, Simon D. Total Synthesis as an Inspiration for Methodology Development: From Natural Products to Novel s-Tetrazines and the Study of Their Reactivity. 2021, University of Zurich, Faculty of Science.

Abstract

Total synthesis has evolved as a valuable tool for the development of novel synthetic compounds and methodologies. We report the synthetic studies towards the polycyclic, complex, marine meroterpe-noid azamerone culminating in the synthesis of two key fragments thereof. Key steps involve a three step diaminoalkylation/oxidation/condensation sequence and the cyclization of enantiomerically en-riched epoxysilanes to synthesize the cyclohexane side-chain of the natural product, with all stereo-centers set. During our synthetic approach we developed 3-bromotetrazine as a minimal tetrazine precursor for the installation of the heterocyclic pyridazine ring of the natural product. Concomi-tantly, 3-bromotetrazine proved to be a precursor for the synthesis of novel classes of 3-monosubsti-tuted s-tetrazines, as a minimal tetrazine surrogate for the installation of bio-orthogonal tetrazines in natural products and proteins and as a precursor for the synthesis of a tetrazine based chemoselective probe. Additional studies aimed at investigating its reactivity towards dienophiles, culminating in insights into the dearomatization reaction of 3-monosubstituted s-tetrazines.

Abstract

Total synthesis has evolved as a valuable tool for the development of novel synthetic compounds and methodologies. We report the synthetic studies towards the polycyclic, complex, marine meroterpe-noid azamerone culminating in the synthesis of two key fragments thereof. Key steps involve a three step diaminoalkylation/oxidation/condensation sequence and the cyclization of enantiomerically en-riched epoxysilanes to synthesize the cyclohexane side-chain of the natural product, with all stereo-centers set. During our synthetic approach we developed 3-bromotetrazine as a minimal tetrazine precursor for the installation of the heterocyclic pyridazine ring of the natural product. Concomi-tantly, 3-bromotetrazine proved to be a precursor for the synthesis of novel classes of 3-monosubsti-tuted s-tetrazines, as a minimal tetrazine surrogate for the installation of bio-orthogonal tetrazines in natural products and proteins and as a precursor for the synthesis of a tetrazine based chemoselective probe. Additional studies aimed at investigating its reactivity towards dienophiles, culminating in insights into the dearomatization reaction of 3-monosubstituted s-tetrazines.

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Additional indexing

Item Type:Dissertation (monographical)
Referees:Gademann Karl, Nevado Blazquez Cristina, Magauer Thomas
Communities & Collections:07 Faculty of Science > Department of Chemistry
UZH Dissertations
Dewey Decimal Classification:540 Chemistry
Language:English
Place of Publication:Zurich
Date:2021
Deposited On:09 Feb 2022 11:22
Last Modified:19 Dec 2023 16:18
OA Status:Closed