727654-69-5

Upstream product

• 5220-49-5 3-amino-cyclohex-2-enone 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 727654-68-4 (Z)-N,N-dimethyl-N'-(3-oxocyclohex-1-en-1-yl)formamidine 
• 504-02-9 1,3-cylohexanedione 

Downstream Products

• 131929-07-2 3,4-diethoxycarbonyl-1,4,5,6,7,8-hexahydroquinol-5-one 
• 827340-31-8 12-benzyl-2,3,4,7,12,13-hexahydro-1H-indolo[3,2-j]phenanthridine-1,7,13-trione 
• 915376-35-1 3,4-dihydro-1H-indolo[3,2-j]phenanthridine-1,7,13(2H,12H)-trione 
• 1021185-94-3 C₂₆H₁₈N₂O₃ 

Relevant academic research and scientific papers

Concise and efficient synthesis of calothrixin B

A convergent synthesis of the naturally occurring alkaloid Calothrixin B is presented, which used a regioselective hetero-Diels-Alder reaction between a "push-pull" 2-aza-diene and a N-protected 3-bromo-9H-carbazole-1,4- dione to construct the five-ring skeleton of the molecule. Protection of the indole motif with a benzyl group was unattractive for delivery of sufficient target material because the removal of the protecting group had not been high yielding. We therefore elected to temporarily protect the indole motif with a more labile benzyloxycarbonyl group. Accordingly, the synthesis of calothrixin B proceeded in 17% overall yield over 9 steps from the commercially available 1,2,3,9-tetrahydro-4H-carbazol-4-one.

A hetero Diels-Alder approach to the synthesis of the first angucyclinone and angucycline 5-aza-analogues

The synthesis of two new heterodienes and their regioselective [4+2]cycloaddition reactions with several bromo-naphthoquinones allowed us to prepare the first angucyclinone and angucycline 5-aza-analogues.