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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Photoactivated [3+2] addition of 6,7-seco-angustilobine B to fullerene [C60]
Allan Patrick G Macabeo1, Dietmar Gehle, Karsten Krohn
1Organic Synthesis and Phytochemistry Laboratory, Research Center for the Natural and Applied Sciences, University of Santo Tomas, Espana, Manila 1015, Philippines. allanpatrick_m@yahoo.com
Abstract:
A synthesis of a new alkaloid-fullerene conjugate (1) is reported. The reaction was carried out by photoinduced [3+2] cycloaddition of the Alstonia indole alkaloid, 6,7-seco-angustilobine B (2), to fullerene[C60] (3) under aerobic conditions. The major monoaddition photoadduct (1) was characterized unambiguously by UV, IR, MALDI-TOFMS and NMR experiments. A mechanism highlighted by sequential photoinduced electron transfer andradical recombination pathways is also proposed. No significant enhancement in inhibition against M. tuberculosis H37Rv was observed for 1 compared with its parent compounds 2 and 3.
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