214119-25-2

Upstream product

• 16618-66-9 2-bromo-6-methoxy-4-nitro-phenylamine 
• 97-52-9 2-methoxy-4-nitrophenylamine 

Downstream Products

• 214119-26-3 2-bromo-6-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine 
• 214119-28-5 N,N'-Diallyl-N,N'-dibenzenesulfonyl-6-bromo-2-methoxy-1,4-phenylenediamine 
• 165817-09-4 Acetic acid 5-(allyl-benzenesulfonyl-amino)-1-benzenesulfonyl-4-iodo-6-methoxy-2,3-dihydro-1H-indol-3-ylmethyl ester 
• 165817-13-0 (1RS)-6-Benzenesulfonyl-3-benzenesulfonyl-5-methoxy-1-acetoxymethyl-8-methylidene-1,2,7,8-tetrahydro-6H-pyrrolo[3,2-e]indole 
• 165817-15-2 (1RS)-6-Benzenesulfonyl-3-benzenesulfonyl-5-methoxy-1-acetoxymethyl-8-methyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole 
• 165817-16-3 (1RS)-6-Benzenesulfonyl-3-benzenesulfonyl-5-hydroxy-1-acetoxymethyl-8-methyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole 
• 165817-07-2 N-Allyl-N-(1-benzenesulfonyl-4-iodo-3-iodomethyl-6-methoxy-2,3-dihydro-1H-indol-5-yl)-benzenesulfonamide 
• 165817-08-3 N-Allyl-N-(1-benzenesulfonyl-3-hydroxymethyl-4-iodo-6-methoxy-2,3-dihydro-1H-indol-5-yl)-benzenesulfonamide 
• 214119-29-6 (1RS)-6-Benzenesulfonyl-3-benzenesulfonyl-5-hydroxy-1-hydroxymethyl-8-methyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole 
• 112793-56-3 (1RS)-3-Benzenesulfonyl-5-hydroxy-1-hydroxymethyl-8-methyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole 
• 608537-12-8 (4RS)-6-[3-butenyl(phenylsulfonyl)amino]-5-iodo-4-iodomethyl-7-methoxy-1-phenylsulfonyl-1,2,3,4-tetrahydroquinoline 
• 608537-14-0 6-[3-butenyl(phenylsulfonyl)amino]-5-iodo-7-methoxy-4-methylene-1-phenylsulfonyl-1,2,3,4-tetrahydroquinoline 
• 608537-15-1 2-bromo-N¹,N⁴-bis(3-butenyl)-6-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine 

Relevant academic research and scientific papers

Synthesis of ring size seco-analogs of the antitumor antibiotic CC-1065 by two consecutive transition metal-initiated transformations

Novel seco-analogs of CC-1065 1 were synthesized from comercially available nitroaniline by reduction, bromination, bisulfonation and bisallylation followed by reaction with tert-butyllithium, zirconocene and iodine. The obtained quinoline 6 was then transformed into 17 and 18, which, upon treatment with Pd0, led to 21 and 22, respectively. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Efficient synthesis of the pharmacophore of the highly potent antitumor antibiotic CC-1065

The pharmacophore CPI (3) of the potent antitumor antibiotic CC-1065 (1) was synthesized in a very short reaction sequence of 11 steps with an overall yield of 23 %. The key steps are two consecutive cyclizations mediated by organotransition metal complexes, which form first the pyrroline and then the pyrrole ring in 3. Thus, halogen metal exchange of the N,N'-bisallylbromobenzene with tBuLi and subsequent reaction with Cp2ZrMeCl gave 11 as a single product in 60 % yield after quenching with two equivalents of iodine. Transformation of the iodomethyl group in 11 into an acetoxymethyl group, followed by Heck reaction, isomerization, and reductive cleavage, provided the pyrroloindoline system 4, which was converted into 3.