Stereoselective Transformations on <scp>d</scp>-Glucose-Derived Eight-Membered Ring Carbocycles

Pa, van Hooft; Re, Litjens; Ga, van der Marel; Ca, van Boeckel; Jh, van Boom

doi:10.1021/ol007047+

Cited by 32 publications

(16 citation statements)

References 20 publications

(19 reference statements)

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“…van Boom and co-workers reported a 1,3-diaxial NOE interaction between 1-H and 7-H in a corresponding derivative, however, we could not verify this. [22] An Xray analysis of a closely related compound confirmed the equatorial orientation of the newly generated hydroxy function after the TIBAL-promoted Claisen rearrangement. [23] Epoxidation with m-chloroperbenzoic acid (MCPBA) and cyclopropanation with the Simmons-Smith reaction [24] (Furukawa modification [25] ) of the functionalized cyclooctenone derivative 26 furnished the optically pure diastereomers 27 and 28, respectively.…”

Section: Resultsmentioning

confidence: 85%

Claisen Rearrangement of Carbohydrate‐Derived Precursors Towards Highly Functionalized Cyclooctenones with L‐xylo, D‐arabino and L‐lyxo Configuration and Their Diastereoselective Transformations

Jürs¹,

Werschkun²,

Thiem³

2006

Eur J Org Chem

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D‐Glucose and D‐mannose have been transformed into precursors incorporating allyl vinyl ether substructures. Both thermally and catalytically, these cyclic allyl vinyl ethers could be converted into the corresponding Claisen rearrangement products. The conformations of these enantiopure 5‐cyclooctenones were studied by NMR spectroscopy and X‐ray crystallography. They proved to be versatile substrates for highly stereo‐ and regioselective modifications. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Section: Resultsmentioning

confidence: 85%

Claisen Rearrangement of Carbohydrate‐Derived Precursors Towards Highly Functionalized Cyclooctenones with L‐xylo, D‐arabino and L‐lyxo Configuration and Their Diastereoselective Transformations

Jürs¹,

Werschkun²,

Thiem³

2006

Eur J Org Chem

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“…Further reductions in catalyst loading were not explored. Scheme 2 ignores irreversible cross metathesis reactions, because we observed no evidence for heterodimeric products at 0.01 M. ‡ Crystallographic data for 16b:C 13 The results in Table 1 also suggest the presence of a modest (less than five-fold) Thorpe-Ingold effect. 26 Murphy and coworkers 27 proposed that a single methyl group placed appropriately could increase RCM yields dramatically; the effect is considerably less clear cut in our system.…”

Section: Synthetic Studiesmentioning

confidence: 81%

Towards novel difluorinated sugar mimetics; syntheses and conformational analyses of highly-functionalised difluorinated cyclooctenones

et al. 2005

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This version is available at https://strathprints.strath.ac.uk/10080/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Highly-functionalised difluorinated cyclooctenones were synthesised from trifluoroethanol using either metallated difluoroenol acetal or carbamate chemistry, followed by a [2,3]-Wittig rearrangement or aldol reaction. Efficient RCM reactions afforded the title compounds which showed rather restricted fluxional behaviour by VT 19 F NMR. Topological characterisation by molecular modelling and NOESY/ROESY experiments offered a number of challenges, but allowed the identification of two favoured boat-chair conformers which interconverted by pseudorotation with relatively large activation barriers.

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“… Synthesis of 5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)-hex-2-enal ( 4 ). In 2001, van Boom et al examined the transformations of D-glucose-derived eight-membered ring carbocycle 5 [ 20 ]. It was found that multistage process involved the formation of densely functional 2-benzyloxysubstituted 2-alkenals 9 ( Scheme 2 ) via a side reaction.…”

Section: Synthesis Of α-Functionally Substituted αβ-Unsaturated Aldehydesmentioning

confidence: 99%

α-Functionally Substituted α,β-Unsaturated Aldehydes as Fine Chemicals Reagents: Synthesis and Application

2021

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α-Functionalized α,β-unsaturated aldehydes is an important class of compounds, which are widely used in fine organic synthesis, biology, medicine and pharmacology, chemical industry, and agriculture. Some of the 2-substituted 2-alkenals are found to be the key metabolites in plant and animal cells. Therefore, the development of efficient methods for their synthesis attracts the attention of organic chemists. This review focusses on the recent advances in the synthesis of 2-functionally substituted 2-alkenals. The approaches to the preparation of α-alkyl α,β-unsaturated aldehydes are not included in this review.

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Stereoselective Transformations on d-Glucose-Derived Eight-Membered Ring Carbocycles

Abstract: [structure: see text]. The cyclooctenol derivative 1 can be transformed into the nine-membered ring lactone 3, as well as the amino-containing carbocycles 4 and 5. The corresponding ketone 2 gives access to the conformationally locked azasugar 6.

Cited by 32 publications

References 20 publications

Claisen Rearrangement of Carbohydrate‐Derived Precursors Towards Highly Functionalized Cyclooctenones with L‐xylo, D‐arabino and L‐lyxo Configuration and Their Diastereoselective Transformations

Claisen Rearrangement of Carbohydrate‐Derived Precursors Towards Highly Functionalized Cyclooctenones with L‐xylo, D‐arabino and L‐lyxo Configuration and Their Diastereoselective Transformations

Towards novel difluorinated sugar mimetics; syntheses and conformational analyses of highly-functionalised difluorinated cyclooctenones

α-Functionally Substituted α,β-Unsaturated Aldehydes as Fine Chemicals Reagents: Synthesis and Application

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