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: purchase@heterocycles.com

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

Paper | Regular issue | Vol 34, No. 6, 1992, pp.1201-1211
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6017
■ A Synthesis of 4-Cyano-hexahydro-2H-benzo[b]quinolizine-7,10-dione as a Simple Model Compound of Saframycin A

Akinori Kubo,* Tatsuya Nakai, Yuichi Koizumi, Naoki Saito, Yuzuru Mikami, Katsukiyo Yazawa, and Jun Uno

*Meiji College of Pharmacy, 1-35-23 Nozawa, Setagaya-ku, Tokyo 154, Japan

Abstract

A simple and efficient synthesis of 4-cyano-8-methoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzo[b]quinolizine-7,10-dione (20a) as a simple model compound of saframycin A (1) is described starting from the corresponding lactam (16). Reduction of the lactam (16) with lithium aluminum hydride followed by sodium cyanide treatment afforded the α-amino nitrile (19) as an inseparable mixture in an excellent yield. Oxidative demethylation of compound (19) with 10N HNO3 gave the title compound (20a) and its C-4 epimer (20b). The structure of 20a was confirmed by 1H nmr and 13C nmr spectroscopic analysis.