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Total Synthesis of the Biscarbazole Alkaloids Murrafoline A–D by a Domino Sonogashira Coupling/Claisen Rearrangement/Electrocyclization Reaction
Author(s) -
Kumar V. Pavan,
Gruner Konstanze K.,
Kataeva Olga,
Knölker HansJoachim
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201305993
Subject(s) - sonogashira coupling , domino , claisen rearrangement , cascade reaction , aryl , chemistry , coupling reaction , stereochemistry , combinatorial chemistry , organic chemistry , palladium , catalysis , alkyl
Why take things one step at a time? Aryl–pyran‐linked biscarbazole alkaloids of the murrafoline group (see crystal structure of murrafoline A; dark gray: C, red: O, blue: N) were accessed readily by a novel domino reaction sequence involving Sonogashira coupling, a Claisen rearrangement, and electrocyclization. The one‐pot procedure enables the straightforward synthesis of these structurally challenging alkaloids in only a few steps.
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