Solution-Phase Parallel Synthesis of Novel Spirooxazolinoisoxazolines

Shih, Han C.; Guo, Chih-Wei; Lo, Kien-Hock; Huang, Min-Yang; Cheng, Wei‐Chieh

doi:10.1021/cc800158t

Cited by 16 publications

(10 citation statements)

References 43 publications

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“…The desired nitrile‐oxide dipole was generated in situ from previously prepared chlorooxime ( 12 ) using triethylamine in dichloromethane , . Pleasingly, this provided isoxazole heterocycle 2 in a 58 % yield with the regio‐chemistry predicted as proposed by transition state TS‐I and similar literature strategies . The highly reactive ester and Boc‐protected amine provide the scope for a wide range of ring‐closing strategies.…”

Section: Resultsmentioning

confidence: 97%

Cycloaddition Strategies for the Synthesis of Diverse Heterocyclic Spirocycles for Fragment‐Based Drug Discovery

et al. 2019

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In recent years the pharmaceutical industry has benefited from the advances made in fragment‐based drug discovery (FBDD) with more than 30 fragment‐derived drugs currently marketed or progressing through clinical trials. The success of fragment‐based drug discovery is entirely dependent upon the composition of the fragment screening libraries used. Heterocycles are prevalent within marketed drugs due to the role they play in providing binding interactions; consequently, heterocyclic fragments are important components of FBDD libraries. Current screening libraries are dominated by flat, sp2‐rich compounds, primarily owing to their synthetic tractability, despite the superior physicochemical properties displayed by more three‐dimensional scaffolds. Herein, we report step‐efficient routes to a number of biologically relevant, fragment‐like heterocyclic spirocycles. The use of both electron‐deficient and electron‐rich 2‐atom donors was explored in complexity‐generating [3+2]‐cycloadditions to furnish products in 3 steps from commercially available starting materials. The resulting compounds were primed for further fragment elaboration through the inclusion of synthetic handles from the outset of the syntheses.

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Section: Resultsmentioning

confidence: 97%

Cycloaddition Strategies for the Synthesis of Diverse Heterocyclic Spirocycles for Fragment‐Based Drug Discovery

et al. 2019

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“…All reaction steps and work‐ups were optimised to allow the use of automatic equipment, including a liquid handler, solution‐phase synthesiser and evaporator. A combinatorial approach has recently accelerated the preparation of natural product analogue libraries, allowing access and the development of biologically useful molecular scaffolds.…”

Section: General Synthetic Strategies From the Chiral Poolmentioning

confidence: 99%

Synthetic Pathways to 3,4,5‐Trihydroxypiperidines from the Chiral Pool

et al. 2018

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3,4,5‐Trihydroxypiperidines represent a family of biologically active natural products, found to modulate principally the glycosidase enzymes. This is ascribed to their structural and electronic resemblance to the pyranose monosaccharides, their natural counterparts. Expedient syntheses are crucial to access these valuable high Fsp3 index drug leads. In this review we present the literature strategies to this class of iminosugars to spur further research into drug leads targeting the glycobiological machinery of living systems.

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“…Several flexible and semiautomated equipment, including a solution-phase synthesizer, multichannel liquid handler, and centrifugal evaporator were used to accelerate the preparation process. Product purification was rapidly accomplished using solid-phase extraction. − …”

Section: Introductionmentioning

confidence: 99%

Rapid Synthesis of a Natural Product-Inspired Uridine Containing Library

Cheng

Liu

et al. 2020

ACS Comb. Sci.

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The preparation of natural product-inspired nucleoside analogs using solution-phase parallel synthesis is described.The key intermediates containing alkyne and N-protected amino moieties were developed to allow for further skeleton and substituent diversity using click chemistry and urea or amide bond formation. Rapid purification was accomplished using solidphase extraction. The obtained library comprised 80 molecules incorporating two diversity positions and one chiral center, each of which was efficiently prepared in good purity and acceptable overall yield. A bacterial morphology study was also performed.

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Solution-Phase Parallel Synthesis of Novel Spirooxazolinoisoxazolines

Cited by 16 publications

References 43 publications

Cycloaddition Strategies for the Synthesis of Diverse Heterocyclic Spirocycles for Fragment‐Based Drug Discovery

Cycloaddition Strategies for the Synthesis of Diverse Heterocyclic Spirocycles for Fragment‐Based Drug Discovery

Synthetic Pathways to 3,4,5‐Trihydroxypiperidines from the Chiral Pool

Rapid Synthesis of a Natural Product-Inspired Uridine Containing Library

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