Literature DB >> 25663720

Total Synthesis of Calothrixins A and B via Oxidative Radical Reaction of Cyclohexenone with Aminophenanthridinedione.

Su Xu1, Thao Nguyen1, Irene Pomilio2, Maria C Vitale2, Sadanandan E Velu3.   

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 7 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.

Entities:  

Keywords:  Aminophenanthridinedione; Calothrixin; Free Radical; Oxidative; Total Synthesis

Year:  2014        PMID： 25663720      PMCID： PMC4313744          DOI： 10.1016/j.tet.2014.06.021

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  25 in total

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