4532-33-6Relevant articles and documents
DIMERIC MURRAYAFOLINE A, A POTENTIAL BIS-CARBAZOLE ALKALOID: 'BIOMIMETIC' SYNTHESIS, ATROPOISOMER SEPARATION, AND ANTIMALARIAL ACTIVITY
Bringmann, Gerhard,Ledermann, Alfons,Francois, Guido
, p. 293 - 300 (1995)
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 chiral phase was developed.Both the mono- and the dimeric phenolic carbazoles displayed in vitro antimalarial activity against Plasmodium falciparum.
New syntheses of murrayafoline-A and murrayaquinone-A via Fischer indolization of 2-sulfonyloxyphenylhydrazone (Fischer indolization and its related compounds. Part 29)
Murakami, Yasuoki,Yokoo, Hiroshi,Watanabe, Toshiko
, p. 127 - 132 (1998)
Two carbazole alkaloids, murrayafoline-A (4a) and murrayaquinone-A (4b), were synthesized from 1, 2, 3, 4-tetrahydro-8-methanesulfonyloxy-6- methylcarbazole (8) prepared in the application of Fischer indolization of 2- sulfonyloxyphenylhydrazone.
Total synthesis of carbazole alkaloids
Bhatthula, Bharath kumar goud,Kanchani, Janardhan reddy,Arava, Veera reddy,Subha
, p. 874 - 887 (2019/01/11)
A Suzuki-Miyaura cross coupling, followed by triphenylphosphine mediated Cadogan reductive cyclization sequence provided efficient access to a series of carbazole alkaloids. In the present work, this approach was applied to the total synthesis of mukonine, clauszoline K, koenoline, murrayanine, murrayafoline A, mukoeic acid, glycoborine, glycozolicine, mukolidine, mukoline, glycozoline, 3-methoxy-9H-carbazole-1-carboxylic acid methyl ester, (3-methoxy-9H-carbazol-1-yl)-methanol, 3-methoxy-9H-carbazole-1-carbaldehyde, 3-methoxy-9H-carbazole-1-carboxylic acid, 2-methyl-9H-carbazole and nonsteroidal anti-inflammatory drug (NSAID) carprofen and its derivatives.
Synthesis of Methylene-Bridged Biscarbazole Alkaloids by using an Ullmann-type Coupling: First Total Synthesis of Murrastifoline-C and Murrafoline-E
Kutz, Sebastian K.,B?rger, Carsten,Schmidt, Arndt W.,Kn?lker, Hans-Joachim
, p. 2487 - 2500 (2016/02/14)
We describe the total synthesis of methylene-bridged biscarbazole alkaloids by using a late-stage Ullmann-type coupling of fully functionalised carbazole subunits. The carbazole derivatives were synthesised via a sequence of palladium(0)- and palladium(II