Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids--first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine.
@article{Gruner2011EfficientIA, title={Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids--first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine.}, author={Konstanze K. Gruner and Thomas Hopfmann and Kazuhiro Matsumoto and Anne J{\"a}ger and Tsutomu Katsuki and Hans‐Joachim Kn{\"o}lker}, journal={Organic \& biomolecular chemistry}, year={2011}, volume={9 7}, pages={ 2057-61 } }
Iron-mediated oxidative cyclisation provides an efficient approach to pyrano[3,2-a]carbazole alkaloids. Thus, improved routes to girinimbine and murrayacine as well as the first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine are reported. Asymmetric epoxidation of girinimbine led to (-)-trans-dihydroxygirinimbine and the assignment of its absolute configuration.
60 Citations
Iron-Mediated Total Synthesis of 2,7-Dioxygenated Carbazole Alkaloids†
- Chemistry
- 2013
We describe the efficient iron-mediated total synthesis of clausine O, clausine H (clauszoline-C) and anti-HIV active 7-methoxy-O-methylmukonal and clausine K (clauszoline-J). Consecutive C–C and C–N…
Total synthesis of 7- and 8-oxygenated pyrano[3,2-a]carbazole and pyrano[2,3-a]carbazole alkaloids via boronic acid-catalyzed annulation of the pyran ring.
- ChemistryChemistry
- 2014
The boronic acid-catalyzed annulation of citral opens up a short route to oxygenated cyclized monoterpenoid pyranocarbazole alkaloids. Thus, murrayamine-D is available in only three steps and 55%…
Palladium(II)-catalysed total synthesis of naturally occurring pyrano[3,2-a]carbazole and pyrano[2,3-b]carbazole alkaloids.
- ChemistryOrganic & biomolecular chemistry
- 2014
Seven naturally occurring pyranocarbazole alkaloids have been obtained by total synthesis using a palladium(II)-catalysed oxidative cyclisation of a diarylamine to an orthogonally diprotected 2,7-dihydroxycarbazole as key step.
Palladium-catalyzed arylation of 2H-chromene: a new entry to pyrano[2,3-c]carbazoles.
- Chemistry, BiologyOrganic & biomolecular chemistry
- 2015
The molecular docking study revealed that this pyrano[2,3-c]carbazole class of molecules selectively occupies the colchicine binding site of the tubulin-polymer.
First Total Synthesis and Investigation of the X-ray Crystal Structure of the Pyrano[3,2-a]carbazole Alkaloid Clausenalansine A
- Chemistry
- 2020
We describe the first total synthesis of the recently discovered pyrano[3,2-a]carbazole alkaloid clausenalansine A. The synthetic strategy for the construction of this formylpyrano[3,2-a]carbazole is…
Synthesis of Methylene-Bridged Biscarbazole Alkaloids by using an Ullmann-type Coupling: First Total Synthesis of Murrastifoline-C and Murrafoline-E.
- ChemistryChemistry
- 2016
This work describes the total synthesis of methylene-bridged biscarbazole alkaloids by using a late-stage Ullmann-type coupling of fully functionalised carbazole subunits through a sequence of palladium(0)- and palladium (II)-catalysed coupling reactions.
Total synthesis of the biscarbazole alkaloids murrafoline A-D by a domino sonogashira coupling/claisen rearrangement/electrocyclization reaction.
- ChemistryAngewandte Chemie
- 2013
Aryl-pyran-linked biscarbazole alkaloids of the murrafoline group were accessed readily by a novel domino reaction sequence involving Sonogashira coupling, a Claisen rearrangement, and electrocyclization, and the one-pot procedure enables the straightforward synthesis of these structurally challenging alkal steroids in only a few steps.
Synthesis of prenyl- and geranyl-substituted carbazole alkaloids by DIBAL-H promoted reductive pyran ring opening of dialkylpyrano[3,2-a]carbazoles.
- ChemistryChemistry
- 2014
In the course of the present work, the DIBAL-H promoted reductive pyran ring opening of dialkylpyrano[3,2-a]carbazoles provides a direct access to a broad range of prenyl- and geranyl-substituted carbazoles.
Total synthesis of the cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids derived from 2-hydroxy-6-methylcarbazole.
- ChemistryOrganic & biomolecular chemistry
- 2014
The synthesis of seven pyrano[3,2-a]carbazole alkaloids has been achieved using their putative biogenetic precursor 2-hydroxy-6-methylcarbazole as key intermediate.
Synthetic Studies for the 1,3‐Iterative Organoiron Approach to the Synthesis of Siculinine: Efficient Arylation Using a Diarylcuprate Reagent
- Chemistry
- 2013
Disubstituted (cyclohexadienyl)iron(1+) complex 2b is prepared by an improved route that starts from 1,2-dimethoxycyclohexa-1,4-diene 3. In five steps, the synthesis of 2b is achieved by complexation…
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Transition Metal Complexes in Organic Synthesis, Part 71: First Total Synthesis of Furoclausine-A
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