First example of carbohydrate-based Prins cyclization: a novel class of sugar-annulated tetrahydropyrans

Yadav, J. S.; Reddy, B. V. Subba; Singh, Ashutosh Pratap; Chaya, Dudhmal N.; Chatterjee, Deepak; Kunwar, A. C.

doi:10.1016/j.tetlet.2010.01.028

Cited by 12 publications

(3 citation statements)

References 25 publications

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“…A Prins–Friedel–Crafts reaction, however, was reported for cis -fused, 4-aryltetrahydropyran in 2011 as a close example (Scheme c) . Prins cyclization for a cis -fused bicyclic ether system has also been reported in 2010 (scheme not shown) . Encouraged by these works, we decided to employ the Prins–Ritter reaction for the preparation of cis -fused 4-amidotetrahydropyrans that can be envisioned as a versatile precursor for dysiherbaine and MC-27 (Figure ).…”

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confidence: 90%

“…10 Prins cyclization for a cis-fused bicyclic ether system has also been reported in 2010 (scheme not shown). 11 Encouraged by these works, we decided to employ the Prins− Ritter reaction for the preparation of cis-fused 4-amidotetrahydropyrans that can be envisioned as a versatile precursor for dysiherbaine 6 and MC-27 8 (Figure 1). This strategy enables one to introduce aryl or vinyl groups to the tetrahydropyran ring of dysiherbaine or MC-27 conveniently, which otherwise requires multistep procedures.…”

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Three-Component, Diastereoselective Prins–Ritter Reaction for cis-Fused 4-Amidotetrahydropyrans toward a Precursor for Possible Neuronal Receptor Ligands

et al. 2016

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Here, we report an unprecedented, highly diastereoselective Prins-Ritter reaction of aldehydes, homoallylic alcohols, and nitriles in a three-component coupling reaction for the synthesis of tetra-cis-substituted 4-amidotetrahydropyrans. In this study, the reaction was not only applied for carbohydrate-based heterobicycles but also for more complex heterotricycles, showing acceptable levels of conversion yield (42-97% BRSM) and exclusive diastereoselectivity. Furthermore, the latter heterotricycles were converted to nine analogues of our neuronal receptor ligands IKM-159 and MC-27. An in vivo assay by intracerebroventricular injection in mice suggested that the substituent at C9 of the novel analogues interferes with the molecular interactions with the AMPA receptor, which was originally observed in the complex of IKM-159 and the GluA2 ligand binding domain. Our research has thus shown the power of a multicomponent coupling reaction for the preparation of a structurally diverse compound collection to study structure-activity relationships of biologically active small molecules.

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Three-Component, Diastereoselective Prins–Ritter Reaction for cis-Fused 4-Amidotetrahydropyrans toward a Precursor for Possible Neuronal Receptor Ligands

et al. 2016

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“…(Figure ). Over the years several methodologies have been developed for the synthesis of tetrahydropyran rings, such as hetero-Diels–Alder reaction, manipulations of carbohydrates, intramolecular oxa-Michael reaction, , cyclization of epoxy alcohols, Prins cyclization, and others . Among the various methods available, Prins cyclization is considered to be the most convenient tool as it forms carbon–carbon and carbon–heteroatom bonds in a single step with high diastereoselectivity. , The major disadvantages of Prins reaction are racemization and side chain exchange leading to the formation of crossover products .…”

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confidence: 99%

Diastereoselective Synthesis of 2,6-Disubstituted Tetrahydropyranones via Prins Cyclization of 3-Bromobut-3-en-1-ols and Aldehydes

et al. 2023

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Tetrahydropyranones are synthesized from 3-bromobut-3-en-1-ols and aldehydes in good yields with excellent diastereoselectivity at −35 °C. The reaction involves an initial formation of a most stable six-membered chairlike tetrahydropyranyl carbocation followed by nucleophilic attack of the hydroxyl group and subsequent elimination of HBr to give tetrahydropyranone. The carbonyl moiety of the tetrahydropyranone is converted to enol ether and esters using Wittig reaction. It is also transformed into 4hydroxy-2,6-disubstituted tetrahydropyran with 2,4-and 4,6-cis configuration by lithium aluminum hydride in up to 96% diastereoselectivity. Furthermore, the methodology is extended toward the synthesis of novel anticancer aminoguanidine compounds.

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Addition Reactions: Polar Addition

Kočovský¹

2012

Organic Reaction Mechanisms Series

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First example of carbohydrate-based Prins cyclization: a novel class of sugar-annulated tetrahydropyrans

Cited by 12 publications

References 25 publications

Three-Component, Diastereoselective Prins–Ritter Reaction for cis-Fused 4-Amidotetrahydropyrans toward a Precursor for Possible Neuronal Receptor Ligands

Three-Component, Diastereoselective Prins–Ritter Reaction for cis-Fused 4-Amidotetrahydropyrans toward a Precursor for Possible Neuronal Receptor Ligands

Diastereoselective Synthesis of 2,6-Disubstituted Tetrahydropyranones via Prins Cyclization of 3-Bromobut-3-en-1-ols and Aldehydes

Addition Reactions: Polar Addition

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