TY  - JOUR
A1  - Kwesiga, George
A1  - Sperlich, Eric
A1  - Schmidt, Bernd
T1  - Scope and applications of 2,3-oxidative aryl rearrangements for the synthesis of isoflavone natural products
T2  - The journal of organic chemistry
N2  - The reaction of flavanones with hypervalent iodine reagents was investigated with a view to the synthesis of naturally occurring isoflavones. In contrast to several previous reports in the literature, we did not observe the formation of any benzofurans via a ring contraction pathway, but could isolate only isoflavones, resulting from an oxidative 2,3-aryl rearrangement, and flavones, resulting from an oxidation of the flavanones. Although the 2,3-oxidative rearrangement allows a synthetically useful approach toward some isoflavone natural products due to the convenient accessibility of the required starting materials, the overall synthetic utility and generality of the reaction appear to be more limited than previous literature reports suggest.
Y1  - 2021
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/56665
SN  - 0022-3263
SN  - 1520-6904
VL  - 86
IS  - 15
SP  - 10699
EP  - 10712
PB  - American Chemical Society
CY  - Washington
ER  -