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Iron‐Mediated Total Synthesis of 2,7‐Dioxygenated Carbazole Alkaloids
Author(s) -
Krahl Micha P.,
Kataeva Olga,
Schmidt Arndt W.,
Knölker HansJoachim
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201251
Subject(s) - chemistry , total synthesis , carbazole , salt (chemistry) , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry
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 bond formations between 3‐methoxy‐4‐methylaniline and a cyclohexadienyliumiron complex salt afforded 2,7‐dimethoxy‐3‐methylcarbazole, which served as common intermediate en route to the four alkaloids.