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 | Special issue | Vol 40, No. 1, 1995, pp.293-300
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S30
■ Dimeric Murrayafoline A, a potential Bis-Carbazole Alkaloid: 'Biomimetic' Synthesis, Atropoisomer Separation, and Antimalarial Activity

Gerhard Bringmann, Alfons Ledermann and Guido François

*Institüte of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany

Abstract

The first total synthesis of a (potential) dimeric carbazole alkaloid is described. After an improved preparation of the monomeric building block, ‘biomimetic dimerization’ by oxidative phenolic coupling was best achieved with di-tert-butyl peroxide in chlorobenzene, leading to a highly selective formation of the 2,2’-coupled ‘dimer’, the parent framework of several naturally occurring dimeric carbazole alkaloids. For the atropoenantiomer analysis, a chromatographic procedure on a chiral phase was developed. Both the mono- and the dimeric phenolic carbazoles displayed in vitro antimalarial activity against Plasmodium falciparum.