The chemical reactivity of a known anti-psoriasis drug. Part 1: Further insights into the products resulting from oxidative cleavage

Alan M. Jones; Magali M. Lorion; Tomas Lebl; Alexandra M. Z. Slawin; Douglas Philp; Nicholas J. Westwood

doi:10.1016/j.tet.2010.10.044

The chemical reactivity of a known anti-psoriasis drug. Part 1: Further insights into the products resulting from oxidative cleavage

Alan M. Jones, Magali M. Lorion, Tomas Lebl, Alexandra M. Z. Slawin, Douglas Philp, Nicholas J. Westwood

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

9 Citations (Scopus)

Abstract

The oxidative cleavage of the known anti-psoriasis drug 1 to give 2 has been reported previously. Due to the importance of accessing medium-sized ring containing systems via oxidative cleavage, this reaction has been revisited revealing additional information about the structure of 2. Alternative reaction products were identified when the reaction was carried out in the presence of water. The conversion of 1 to 2 has also been carried out using ruthenium tetroxide. A detailed variable temperature NMR and computational study of the restricted rotation of the N-aryl ring in 2 is presented. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	9667-9674
Number of pages	8
Journal	Tetrahedron
Volume	66
Issue number	51
DOIs	https://doi.org/10.1016/j.tet.2010.10.044
Publication status	Published - 18 Dec 2010

Keywords

Heterocycle
Oxidative fragmentation
Macrocycle
VT NMR analysis
Mechanism
COMPLEXES
OLEFINS
DIOLS
DIONE

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10.1016/j.tet.2010.10.044

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title = "The chemical reactivity of a known anti-psoriasis drug. Part 1: Further insights into the products resulting from oxidative cleavage",

abstract = "The oxidative cleavage of the known anti-psoriasis drug 1 to give 2 has been reported previously. Due to the importance of accessing medium-sized ring containing systems via oxidative cleavage, this reaction has been revisited revealing additional information about the structure of 2. Alternative reaction products were identified when the reaction was carried out in the presence of water. The conversion of 1 to 2 has also been carried out using ruthenium tetroxide. A detailed variable temperature NMR and computational study of the restricted rotation of the N-aryl ring in 2 is presented. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "Heterocycle, Oxidative fragmentation, Macrocycle, VT NMR analysis, Mechanism, COMPLEXES, OLEFINS, DIOLS, DIONE",

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T1 - The chemical reactivity of a known anti-psoriasis drug. Part 1: Further insights into the products resulting from oxidative cleavage

AU - Jones, Alan M.

AU - Lorion, Magali M.

AU - Lebl, Tomas

AU - Slawin, Alexandra M. Z.

AU - Philp, Douglas

AU - Westwood, Nicholas J.

PY - 2010/12/18

Y1 - 2010/12/18

N2 - The oxidative cleavage of the known anti-psoriasis drug 1 to give 2 has been reported previously. Due to the importance of accessing medium-sized ring containing systems via oxidative cleavage, this reaction has been revisited revealing additional information about the structure of 2. Alternative reaction products were identified when the reaction was carried out in the presence of water. The conversion of 1 to 2 has also been carried out using ruthenium tetroxide. A detailed variable temperature NMR and computational study of the restricted rotation of the N-aryl ring in 2 is presented. (C) 2010 Elsevier Ltd. All rights reserved.

AB - The oxidative cleavage of the known anti-psoriasis drug 1 to give 2 has been reported previously. Due to the importance of accessing medium-sized ring containing systems via oxidative cleavage, this reaction has been revisited revealing additional information about the structure of 2. Alternative reaction products were identified when the reaction was carried out in the presence of water. The conversion of 1 to 2 has also been carried out using ruthenium tetroxide. A detailed variable temperature NMR and computational study of the restricted rotation of the N-aryl ring in 2 is presented. (C) 2010 Elsevier Ltd. All rights reserved.

KW - Heterocycle

KW - Oxidative fragmentation

KW - Macrocycle

KW - VT NMR analysis

KW - Mechanism

KW - COMPLEXES

KW - OLEFINS

KW - DIOLS

KW - DIONE

U2 - 10.1016/j.tet.2010.10.044

DO - 10.1016/j.tet.2010.10.044

M3 - Article

SN - 0040-4020

VL - 66

SP - 9667

EP - 9674

JO - Tetrahedron

JF - Tetrahedron

IS - 51

ER -

The chemical reactivity of a known anti-psoriasis drug. Part 1: Further insights into the products resulting from oxidative cleavage

Abstract

Keywords

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