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

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.

SUBMITTER: Xu S 

PROVIDER: S-EPMC4313744 | biostudies-other | 2014 Sep

REPOSITORIES: biostudies-other

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

Xu Su S   Nguyen Thao T   Pomilio Irene I   Vitale Maria C MC   Velu Sadanandan E SE  

Tetrahedron 20140901 35

Bioactive indolo[3,2-<i>j</i>]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)<sub>3</sub> mediated oxidative free radical reaction of 9-(benzylamino)phenanthridine -7,10-dione with cyclohexenone to form 12-benzyl-12<i>H-</i>indolo[3,2-<i>j</i>]phenanthri  ...[more]

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