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Showing 1 to 15 of 15 for “"iterative cross-coupling"”.
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Iterative cross-coupling with MIDA boronates
… approach to small molecule making based on the iterative cross-coupling (ICC) of bifunctional haloboronic acid building blocks. Realizing a general ICC approach in the context of small molecule synthesis required the discovery of a ligand with the capacity to attenuate the reactivity of boronic …
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Semisynthesis of amphotericin B and its derivatives via iterative cross-coupling
… synthesis of polyene natural products via the iterative Suzuki-Miyaura cross-coupling of bifunctional polyenyl MIDA boronate building blocks. This methodology was taken on to complete efficient total syntheses of all-trans-retinal, β-parinaric acid, and one half of AmB. In order to validate …
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An iterative cross-coupling based approach to the synthesis of peridinin and progress towards peridinin derivatives
… development of a stereoretentive Suzuki-Miyaura coupling of haloallenes.
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Expansion and automation of iterative cross-coupling: total synthesis of synechoxanthin and development of a small molecule synthesizer
Item withdrawn by Mark Zulauf (zulauf@illinois.edu) on 2014-04-15T20:00:36Z Item was in collections: University of Illinois Theses & Dissertations (ID: 1) No. of bitstreams: 1 Sisco_Seiko.pdf: 39731093 bytes, checksum: c5a677f96924a2150cc9bc68dfe0cc54 (MD5)
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Expansion of the iterative cross-coupling synthesis strategy through Csp3 halide cross-coupling, Mida boronate synthesis, and chan-lam couplings
The iterative cross-coupling strategy for small molecule synthesis has been shown to be a powerful and effective method for the synthesis of small molecules. However, this strategy was limited by current methodological limitations. Therefore, we have extended the power and application of the …
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Design of a second generation MIDA boronate: iterating c(sp3) based Suzuki cross couplings
… and other biomolecules, we have pioneered iterative cross coupling (ICC) as an analogous platform for small molecules. Enabled by both a building block based synthesis strategy and a general purification protocol, our group has designed and built a small molecule synthesizer. We have …
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Stereospecific Csp3 cross-coupling for modular polyketide synthesis
Iterative cross-coupling represents a simple strategy for the synthesis of functional molecules that is inherently automatable. However, an important limitation to this platform is an inability to generate Csp3-rich, stereochemically complex molecules due to challenges in the coupling of alkyl …
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A small molecule synthesizer
… C-C bond forming reaction, the Suzuki-Miyaura cross-coupling (SMC) reaction, to assemble off-the-shelf building blocks into many different types of small molecules including organic materials, pharmaceuticals, natural products, and natural product derivatives. Specifically, this automated …
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Slow-release cross-coupling and an advanced method for β-glycosylation: methods stimulated by amphotericin B
… in the construction of the AmB polyene, a new cross-coupling protocol was developed whereby N-methyliminodiacetic acid (MIDA) boronates can be used directly in Suzuki-Miyaura cross-coupling (SMC) reactions, enabling air-stable MIDA boronates to act as surrogates for boronic acids. Additionally, …
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Total synthesis and study of the antilipoperoxidant peridinin, synthesis of versatile MIDA boronate building blocks, and a general strategy for the synthesis of polyenes
… a building block based approach involving the iterative cross-coupling of MIDA boronate containing molecules can be a universal platform for the preparation of small molecules. Guided by this strategy we completed an efficient, flexible, and fully stereocontrolled synthesis of the carotenoid …
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Part I: synthesis and cross-coupling of the C1-C12 primary organoborane building block of amphotericin B; Part II: site- and stereoretentive cross-coupling of unactivated secondary boronic acids inspired by amphotericin B
… are readily assembled using only a single cross-coupling reaction repeatedly. Such an iterative cross-coupling (ICC) strategy has been applied in our proposed total synthesis of clinically valuable polyene natural product amphotericin B (AmB). In our retrosynthetic analysis, AmB is …
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Synthesis and function of the conserved motif of mycosamine-containing polyene macrolides
… platform for small molecule synthesis based on iterative cross-coupling. This synthesis was enabled by the development of a new type of diastereotopic group-selective lactonization and a new directing group for the challenging installation of the mycosamine sugar. This building block may help …
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Low-temperature protonation studies of an electron-poor osmium methyl complex, and molecular precursors for the construction of graphene nanostructues with atomically precise edge structures
… a binomial quintet in the 13C NMR with a coupling constant (127 Hz) almost identical to that of free methane (125 Hz). Kinetic analysis revealed that the enthalpy and entropy of activation for methane loss was ΔH‡ = 14.9 ± 1.5 kcal mol-1 and ΔS‡ = 12.3 ± 8.8 cal mol-1 K-1, respectively, …
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Less toxic yet still resistance evasive amphotericins and atomistic probing of the amphotericin B ion channel
… synthesis of AmB was designed grounded in the iterative cross coupling (ICC) strategy for small molecule synthesis. The synthesis was divided into three main phases, building block construction, ICC, and protecting group removal. Advances were made in all three phases. A scalable synthesis of …
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Closed-loop iterative molecular discovery engines
Submission published under a 24 month embargo labeled 'Closed Access', the embargo will last until 2025-08-01