Total synthesis of calothrixins A and B via oxidative radical reaction of cyclohexenone with aminophenanthridinedione

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 synt...

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Bibliographic Details
Published in:Tetrahedron 2014-09, Vol.70 (35), p.5928-5933
Main Authors: Xu, Su, Nguyen, Thao, Pomilio, Irene, Vitale, Maria C., Velu, Sadanandan E.
Format: Article
Language:English
Subjects:
Alkaloids
Aminophenanthridinedione
Biocompatibility
Calothrixin
chemical reactions
chemical structure
Derivatives
Free radical
Free radicals
manganese
Oxidative
Radicals
Synthesis (chemistry)
Tetrahedrons
Total synthesis
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.06.021