TY - JOUR
T1 - The chemical reactivity of a known anti-psoriasis drug. Part 1
T2 - Further insights into the products resulting from oxidative cleavage
AU - Lorion, Magali M.
AU - Lebl, Tomas
AU - Slawin, Alexandra M Z
AU - Philp, Douglas
AU - Westwood, Nicholas J.
AU - Jones, Alan
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.
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.
KW - Heterocycle
KW - Macrocycle
KW - Mechanism
KW - Oxidative fragmentation
KW - VT NMR analysis
UR - http://www.scopus.com/inward/record.url?scp=78650191635&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2010.10.044
DO - 10.1016/j.tet.2010.10.044
M3 - Article
AN - SCOPUS:78650191635
SN - 0040-4020
VL - 66
SP - 9667
EP - 9674
JO - Tetrahedron
JF - Tetrahedron
IS - 51
ER -