Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Regular issue | Vol 14, No. 6, 1980, pp.799-807
Published online, 1st January, 1970
DOI: 10.3987/R-1980-06-0799
Synthesis of a Potential Intermediate to apo-Mitomycins

Tetsuji Kametani,* Yoshio Kigawa, Hideo Nemoto, Masataka Ihara, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Cyclisation of compound (8), which was obtained by condensation of benzyl α-bromo-α-(2-bromo-5-methoxy-4-methylphenyl)acetare (7) with trans-3-acetoxy-4-(N-ethoxycarbonyl-N-methylamino)-2-thiopyrrolidone (2), afforded pyrroloindoles (9) and (10), the former of which on hydrogenolysis gave carboxylic acid (11). Carboxaldehyde (13), which was synthesised from (11) via thioester (12) by successive treatment with oxalyl chloride and ethyl mercaptan, was converted into nitro compound (15). Finally reduction of (15) followed by oxidation of resulting amino compound (16) furnished (±)-1α-acetoxy-2β-[N-ethoxycarbonyl-N-methylamino]-2,3-dihydro-7-methoxy-6-methyl-5,8-dioxo-1H-pyrrolo[1,2-a]indole-9-carboxaldehyde (17).