Total synthesis of calothrixins A and B via oxidative radical reaction of cyclohexenone with aminophenanthridinedione |
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| Authors: | Su Xu Thao Nguyen Irene Pomilio Maria C. Vitale Sadanandan E. Velu |
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| Affiliation: | 1. Department of Chemistry, University of Alabama at Birmingham, 901 14th Street South, Birmingham, AL 35294-1240, USA;2. Comprehensive Cancer Center, University of Alabama at Birmingham, 1720 2nd Avenue South, Birmingham, AL 35294-3300, USA;3. Exchange Program Students from the University of “G. d''Annunzio” Chieti-Pescara, Via dei Vestini, 66013 Chieti, Italy |
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| Abstract: | Bioactive indolo[3,2-j]phenanthridine alkaloids, calothrixin B and its N-oxide derivative calothrixin A have been synthesized via an oxidative free radical reaction. Calothrixin B is generated from the commercially available 2,4,5-trimethoxybenzaldehyde in only seven steps. The key step in this synthesis is the Mn(OAc)3 mediated oxidative free radical reaction of 9-(benzylamino)phenanthridine-7,10-dione with cyclohexenone to form 12-benzyl-12H-indolo[3,2-j]phenanthridine-7,13-dione. |
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| Keywords: | Calothrixin Total synthesis Oxidative Free radical Aminophenanthridinedione |
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