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Synthesis of Glycoborine, Glybomine A and B, the Phytoalexin Carbalexin A and the β‐Adrenoreceptor Antagonists Carazolol and Carvedilol
Author(s) -
Brütting Christian,
Hesse Ronny,
Jäger Anne,
Kataeva Olga,
Schmidt Arndt W.,
Knölker HansJoachim
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604002
Subject(s) - phytoalexin , carvedilol , chemistry , stereochemistry , pharmacology , combinatorial chemistry , medicine , heart failure , resveratrol
Abstract We describe a regioselective synthesis of 4‐ or 5‐substituted carbazoles by oxidative cyclisation of meta ‐oxygen‐substituted N ‐phenylanilines. Using the regiodirecting effect of a pivaloyloxy group, we prepared 4‐hydroxycarbazole, a precursor for the enantiospecific synthesis of the β‐adrenoreceptor antagonists (−)‐( S )‐carazolol ( 5 ) and (−)‐( S )‐carvedilol ( 6 ). Regioselective palladium(II)‐catalysed cyclisation of different diarylamines led to total synthesis of glycoborine ( 7 ) and the first total syntheses of the phytoalexin carbalexin A ( 8 ), glybomine A ( 9 ) and glybomine B ( 10 ). For glybomine B ( 10 ), a 5‐hydroxycarbazole was converted into the corresponding triflate and utilized for introduction of a prenyl substituent.