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Showing papers on "Ferrier rearrangement published in 1991"

Journal Article•DOI•
Synthesis of enantiomerically pure, P-1-tethered inositol tetrakis(phosphate) affinity labels via a Ferrier rearrangement

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Virginia A. Estevez1, Glenn D. Prestwich1•
Stony Brook University1
01 Dec 1991-Journal of the American Chemical Society

85 citations

Journal Article•DOI•
Stereoselective total synthesis of (+)-lycoricidine

[...]

Noritaka Chida1, Masami Ohtsuka1, Seiichiro Ogawa1•
Keio University1
01 Jan 1991-Tetrahedron Letters
TL;DR: In this paper, the stereoselective total synthesis of the title compound starting from D-glucose is described, and the key steps in this synthesis are Ferrier rearrangement to construct the optically active cyclohexenone (C-ring), and Pd-catalyzed intramolecular Heck reaction to build the phenanthridone skeleton.

68 citations

Journal Article•DOI•
Synthesis of optically active substituted cyclohexenones from carbohydrates by catalytic Ferrier rearrangement

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Noritaka Chida, Masami Ohtsuka, Katsuyuki Ogura, Seiichiro Ogawa
01 Jul 1991-Bulletin of the Chemical Society of Japan
TL;DR: In this paper, the conversion of hex-5-enopyranosides into substituted cyclohexanones (Ferrier rearrangement) was found to proceed efficiently with a catalytic amount of various mercury(II) salts at room temperature in a neutral solvent system.
Abstract: Conversion of hex-5-enopyranosides into substituted cyclohexanones (Ferrier rearrangement) was found to proceed efficiently with a catalytic amount of various mercury(II) salts at room temperature in a neutral solvent system. Among the mercury(II) salts tested, mercury(II) trifluoroacetate showed the highest activity. Four optically active cyclohexenones were prepared from hex-5-enopyranosides utilizing this method.

52 citations

Journal Article•DOI•
Direct Preparation of 2‐Deoxy‐D‐glucopyranosides from Glucals without Ferrier Rearrangement.

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Véronique Bolitt1, Charles Mioskowski1, Sang Gyeong Lee1, John R. Falck1•
Centre national de la recherche scientifique1
23 Apr 1991-ChemInform
TL;DR: In this paper, an efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is described.
Abstract: An efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is described

15 citations

Patent•
Route to glycals in the allal and gulal series

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Randall L. Halcomb1, Samuel J. Danishefsky1, Mark D. Wittman1•
Yale University1
22 Mar 1991
TL;DR: In this paper, axial anomeric sulfoxides generated via thiophenol Ferrier rearrangement of glucal and galactal derivatives are used to synthesize glycals of the gulal and allal series.
Abstract: Axial anomeric sulfoxides generated via thiophenol Ferrier rearrangement of glucal and galactal derivatives are used to synthesize glycals of the gulal and allal series. An application of the method led to the synthesis of the esperamicin thiosugar.

1 citations