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Total Synthesis of Carbazomycin G
Author(s) -
Chakraborty Suchandra,
Saha Chandan
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.201300467
Subject(s) - chemistry , regioselectivity , carbazole , methyllithium , diazomethane , acetylation , medicinal chemistry , cerium , nucleophile , total synthesis , derivative (finance) , catalysis , organic chemistry , hydrolysis , quinone , biochemistry , financial economics , economics , gene
A concise total synthesis of carbazomycin G has been completed in five steps. Cerium(IV) ammonium nitrate (CAN)–SiO 2 ‐mediated oxidation of 2‐methyl‐2,3,4,9‐tetrahydro‐1 H ‐ carbazol‐1‐one afforded a carbazole‐1,4‐quinone derivative, 2‐methyl‐1 H ‐carbazole‐1,4(9 H )‐dione, the synthetic precusor, which on, which, on Thiele acetylation under newly developed HBF 4 catalysis conditions, yielded 4‐hydroxy‐2‐methyl‐9 H ‐carbazole‐1,3‐diyl diacetate. Finally, CAN‐SiO 2 ‐mediated oxidative hydrolysis of the acetylation product and O ‐methylation using a stoichiometric amount of diazomethane and subsequent regioselective nucleophilic addition of methyllithium led to carbazomycin G.