Preparation of novel polysubstituted chiral cyclohexanone derivatives containing a quaternary carbon by Ferrier reaction

Hladezuk, Isabelle; Olesker, Alain; Tchertanov, Luba; Cléophax, J.

doi:10.1016/s0008-6215(00)00274-3

Cited by 7 publications

(3 citation statements)

References 20 publications

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“…Besides the studies on catalysts of mercury salts in Ferrier II reaction, Hladezuk et al [30] studied the effects on the structures of carbohydrate derivatives. Among ringconversion precursors 61, 62, and 63, it was found that when 61 was submitted to the reaction with mercury salts, no carbocyclic product was obtained regardless of the use of mercury chloride or mercury trifluoroacetate.…”

Section: Ferrier II R Earrangement Promoted By Mercury (Ii) Saltsmentioning

confidence: 99%

From Exocyclic-Olefinic Carbohydrate Derivatives to Functionalized Carbocyclic Compounds

Zhou¹,

Wang²,

Zhang³

et al. 2006

COC

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As the structural constituents of many naturally occurring molecules, synthesis of functionalized carbocyclic derivatives has been widely investigated. Among numerous approaches to construct carbocyclic compounds, there is an efficient way of forming carbocyclic derivatives by the use of various monosaccharides as chiral building blocks. In this review, synthetic conversions to functionalized carbocyclic compounds from exocyclic-olefinic saccharides and their applications to synthesis of some natural products or natural product-like analogues will be discussed. The emphases will be put on the latest methodology developments of ring-conversion rearrangement reactions catalyzed by metal catalysts.

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Section: Ferrier II R Earrangement Promoted By Mercury (Ii) Saltsmentioning

confidence: 99%

From Exocyclic-Olefinic Carbohydrate Derivatives to Functionalized Carbocyclic Compounds

Zhou¹,

Wang²,

Zhang³

et al. 2006

COC

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“…8,9 Many important compounds have been synthesized using Ferrier carbocyclization and its modifications. [10][11][12][13][14][15][16][17][18][19][20][21][22] Conformational characteristics of the pyranose ring are important and have been investigated in considerable depth because the biological and chemical functions of carbohydrates are intimately related to their conformational properties. [23][24][25][26] The conformations of 6-deoxyhex-5-enopyranosides undoubtedly play a significant role in the stereochemistry of the ringclosure reaction during carbocyclization.…”

Section: Introductionmentioning

confidence: 99%

“…Some of these antibiotics exhibit impressive activities against a broad range of solid tumors and soft-tissue sarcomas . Additionally, 6-deoxyhex-5-enopyranosides are substrates in Ferrier carbocyclization, the most common reaction for preparing chiral-substituted cyclohexanones from aldohexoses. , Many important compounds have been synthesized using Ferrier carbocyclization and its modifications. − …”

Section: Introductionmentioning

confidence: 99%

Methyl 4-O-Acetyl-3-azido- and 3-Azido-4-O-methylsulfonyl-2,3,6,-trideoxyhex-5- enopyranosides in DFT-Level Conformational Studies

Nowacki

Liberek

2007

J. Phys. Chem. A

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Geometry optimizations at the B3LYP level of density functional theory (DFT) are reported for methyl 4-O-acetyl-3-azido- and 3-azido-4-O-methylsulfonyl-2,3,6-trideoxy-alpha,beta-d-threo- and -beta-d-erythro-hex-5-enopyranosides. The most stable conformers for each compound are presented, along with the corresponding enthalpies and Gibbs free energies. The influence of the exocyclic double bond on the chair conformation is discussed. Conformations of the 1-OMe, 3-N3, and 4-OAc groups were examined, and delocalization in the OAc and N3 groups was demonstrated. The contributions of particular conformers to the total number of structures found for each hex-5-enopyranoside were calculated. The theoretical results are compared with assignments based on 1H NMR studies.

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Ferrier‐II Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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The mercury (II) salt‐induced or promoted conversion of 5‐enopyranosides into cyclohexanones with stereochemical control, by which substituents at positions 3 and 5 are predominantly in a trans relationship, is known as the Ferrier‐II rearrangement. This reaction has proven valuable in preparation of carbosugars, myo ‐inositols, and other natural products.

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Preparation of novel polysubstituted chiral cyclohexanone derivatives containing a quaternary carbon by Ferrier reaction

Cited by 7 publications

References 20 publications

From Exocyclic-Olefinic Carbohydrate Derivatives to Functionalized Carbocyclic Compounds

From Exocyclic-Olefinic Carbohydrate Derivatives to Functionalized Carbocyclic Compounds

Methyl 4-O-Acetyl-3-azido- and 3-Azido-4-O-methylsulfonyl-2,3,6,-trideoxyhex-5- enopyranosides in DFT-Level Conformational Studies

Ferrier‐II Rearrangement

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