1072127-10-6Relevant articles and documents
Total syntheses of murrayamine E, I, and K
Schuster, Christian,Julich-Gruner, Konstanze K.,Schnitzler, Heinrich,Hesse, Ronny,J?ger, Anne,Schmidt, Arndt W.,Kn?lker, Hans-Joachim
, p. 5666 - 5673 (2015)
We describe efficient synthetic routes to murrayamine A (mukoenine C), O-methylmurrayamine A, mahanine, O-methylmahanine, and murrayamine D and the first total syntheses of murrayamine E, I, and K. Key steps are a palladium-catalyzed construction of the carbazole framework and an annulation of the pyran ring, which is either catalyzed by phenylboronic acid or promoted by a Lewis acid.
Efficient construction of pyrano [3, 2-a]carbazoles: Application to a biomimetic total synthesis of cyclized monoterpenoid pyrano [3, 2-a]carbazole Alkaloids
Hesse, Ronny,Gruner, Konstanze K.,Kataeva, Olga,Schmidt, Arndt W.,Kn?lker, Hans-Joachim
, p. 14098 - 14111 (2013)
We have developed a highly efficient route to 2-hydroxy-3-methyl-carbazole (1) via a palladium-catalyzed construction of the carbazole skeleton. Using 1 as relay compound, different methods for annulations of pyran rings by reaction with terpenoid building blocks have been tested. The Lewis acid promoted reaction of 1 with prenal (21) opened up an efficient route to girinimbine (3) and the corresponding reaction with citral (25) afforded mahanimbine (5). Oxidation of compounds 3 and 5 provided murraya-cine (4) and murrayacinine (6). Following the biogenetic proposal, mahanim-bine (5) has been exploited for efficient biomimetic syntheses of the cyclized monoterpenoid pyrano[3, 2-a]carbazole alkaloids cyclomahanimbine (7), maha-nimbidine (8) and bicyclomahanimbine (9). The interconversions of 5, 7, 8 and 9 are described and mechanistic implications are discussed. Structural assignments are unambiguously verified by X-ray crystal structure determinations. Moreover, cyclomahanimbine (7) was transformed into murrayazolinine (10) and exozoline (11).
Total synthesis of the biscarbazole alkaloids murrafolinea a-d by a domino sonogashira coupling/claisen rearrangement/electrocyclization reaction
Kumar, V. Pavan,Gruner, Konstanze K.,Kataeva, Olga,Knoelker, Hans-Joachim
, p. 11073 - 11077 (2013)
Why take things one step at a time? Aryl-pyran-linked biscarbazole alkaloids of the murrafoline group (see crystal structure of murrafolinea A; dark gray: C, red: O, blue: N) were accessed readily by a novel domino reaction sequence involving Sonogashira
Enantiospecific total syntheses and assignment of absolute configuration of cannabinol-skeletal carbazole alkaloids murrayamines-O and -P
Dethe, Dattatraya H.,Das, Saikat,Dherange, Balu D.,Mahapatra, Samarpita
supporting information, p. 8347 - 8350 (2015/06/02)
First enantiospecific total syntheses of the cannabinol-skeletal carbazole alkaloids murrayamines-O and -P isolated from root barks of Murraya euchrestifoli, have been accomplished by highly diastereoselective, Lewis acid catalyzed coupling reactions of commercially available monoterpenes with carbazole derivative, which in addition to confirming the structure also established the absolute configuration of the natural products. Synthesis of both natural products and their enantiomers was achieved with high atom economy, in a protecting-group free manner and in six steps longest linear sequence from commercially available aniline derivative and verbenol.
Acid-free synthesis of carbazoles and carbazolequinones by intramolecular Pd-catalyzed, microwave-assisted oxidative biaryl coupling reactions efficient syntheses of murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine
Sridharan, Vellaisamy,Antonia Martin,Carlos Menendez
supporting information; experimental part, p. 4614 - 4621 (2009/12/05)
A mild and. efficient methodology for the synthesis of oxygenated. carbazoles from diarylamines under non-acidic conditions was developed, based on a palladium-catalyzed, microwave-assisted double C-H bond activation process. This new protocol was successfully applied to the synthesis of three naturally occurring carbazoles, namely murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine. The scope of the reaction was also expanded, to include the synthesis of benzo fused carbazolequinones. Wiley-VCH Verlag GmbH & Co. KGaA.
Transition metals in organic synthesis, Part 87:1 An efficient palladium-catalyzed route to 2-oxygenated and 2,7-dioxygenated carbazole alkaloids - Total synthesis of 2-methoxy-3-methylcarbazole, glycosinine, clausine L, mukonidine, and clausin
Forke, Ronny,Krahl, Micha P.,D?britz, Frank,J?ger, Anne,Kn?lker, Hans-Joachim
scheme or table, p. 1870 - 1876 (2009/04/08)
Optimization of the palladium(II)-catalyzed oxidative cyclization of N,N-diarylamines opens up the way to an efficient synthesis of 2-oxygenated and 2,7-dioxygenated carbazole alkaloids including 2-methoxy-3-methylcarbazole, glycosinine, clausine L, mukon
