Studies toward the Synthesis of Oximidines I and II

Torsten Haack; Serdar Kurtkaya; James P. Snyder; Gunda I. Georg

doi:10.1021/ol036007d

Studies toward the Synthesis of Oximidines I and II

Torsten Haack, Serdar Kurtkaya, James P. Snyder, Gunda I. Georg

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

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Abstract

(Equation presented) The synthesis of compound 1, a precursor for the synthesis of the oximidine II core structure 2, is described. An undesired C8-C9 isomerization occurred during the intramolecular Castro-Stephens reaction leading to macrocyle 3. The thermodynamic driving force for this unexpected isomerization was established by DFT and MP2 calculations.

Original language	English (US)
Pages (from-to)	5019-5022
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	26
DOIs	https://doi.org/10.1021/ol036007d
State	Published - Dec 25 2003

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@article{120294f03f17420c972189b1d9d35c9f,

title = "Studies toward the Synthesis of Oximidines I and II",

abstract = "(Equation presented) The synthesis of compound 1, a precursor for the synthesis of the oximidine II core structure 2, is described. An undesired C8-C9 isomerization occurred during the intramolecular Castro-Stephens reaction leading to macrocyle 3. The thermodynamic driving force for this unexpected isomerization was established by DFT and MP2 calculations.",

author = "Torsten Haack and Serdar Kurtkaya and Snyder, {James P.} and Georg, {Gunda I.}",

year = "2003",

month = dec,

day = "25",

doi = "10.1021/ol036007d",

language = "English (US)",

volume = "5",

pages = "5019--5022",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "26",

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T1 - Studies toward the Synthesis of Oximidines I and II

AU - Haack, Torsten

AU - Kurtkaya, Serdar

AU - Snyder, James P.

AU - Georg, Gunda I.

PY - 2003/12/25

Y1 - 2003/12/25

N2 - (Equation presented) The synthesis of compound 1, a precursor for the synthesis of the oximidine II core structure 2, is described. An undesired C8-C9 isomerization occurred during the intramolecular Castro-Stephens reaction leading to macrocyle 3. The thermodynamic driving force for this unexpected isomerization was established by DFT and MP2 calculations.

AB - (Equation presented) The synthesis of compound 1, a precursor for the synthesis of the oximidine II core structure 2, is described. An undesired C8-C9 isomerization occurred during the intramolecular Castro-Stephens reaction leading to macrocyle 3. The thermodynamic driving force for this unexpected isomerization was established by DFT and MP2 calculations.

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DO - 10.1021/ol036007d

M3 - Article

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AN - SCOPUS:0347286690

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VL - 5

SP - 5019

EP - 5022

JO - Organic Letters

JF - Organic Letters

IS - 26

ER -

Studies toward the Synthesis of Oximidines I and II

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