1375488-01-9

Upstream product

• 67-56-1 methanol 
• 1375488-00-8 9-benzyl-(4-benzyloxy)-1-bromo-9H-carbazole-3-carbaldehyde 
• 1375487-99-2 1-bromo-4-hydroxy-9H-carbazole-3-carbaldehyde 
• 1375487-97-0 4-hydroxy-9H-carbazole-3-carbaldehyde 

Downstream Products

• 1375488-02-0 (9-benzyl-1,4-dimethoxy-9H-carbazol-3-yl)methanol 
• 1375488-03-1 N-[(9-benzyl-1,4-dimethoxy-9H-carbazol-3-yl)methyl]-2-iodoaniline 
• 1375488-04-2 N-[(9-benzyl-1,4-dimethoxy-9H-carbazol-3-yl)methyl]-N-(2-iodophenyl)acetamide 
• 1375488-05-3 1-(12-benzyl-7,13-dimethoxy-6H,12H-5,12-diazaindeno[1,2-b]phenanthren-5-yl)-ethanone 
• 827340-35-2 12-benzyl-12H-5,12-diazaindeno[1,2-b]phenanthrene-7,13-dione 

Relevant academic research and scientific papers

An efficient total synthesis of calothrixin B

An efficient synthesis of calothrixin B (2) is demonstrated starting from 9H-carbazol-4-ol, having two one-pot reaction sequences as key steps. As a novel observation, DMF-methanol was shown to be a hydride donor for reduction of aldehyde to alcohol. Unexpectedly, nucleophilic substitution of benzyloxy by methoxy group was observed.

Unexpected observations during the total synthesis of calothrixin B-sodium methoxide as a source of hydride

During the total synthesis of calothrixin B, various novel and unexpected results were noticed such as cleavage of C-N bond in imine using sodium cyanoborohydride, sodium methoxide as a hydride source for reduction, deformylation in the presence of bromine, and deacylation using ceric ammonium nitrate (CAN). A detailed mechanism has been proposed for the unexpected results and a few of them are generalized. Temperature dependent NMR studies have been carried out for confirmation of the structure of one of the intermediates in the synthetic sequence.