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Regioselective Alkylation of 1,4,5‐Trihydroxy‐9,10‐anthraquinone with Formaldehyde and Glyoxylic Acid
Author(s) -
Krohn Karsten
Publication year - 1979
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197906211
Subject(s) - glyoxylic acid , chemistry , anthraquinone , regioselectivity , alkylation , formaldehyde , intramolecular force , ring (chemistry) , organic chemistry , medicinal chemistry , catalysis
The ring system of the cytostatically active anthracycline antibiotics is being increasingly synthesized by intramolecular cylization. Reaction of (1) with glyoxylic acid, reduction and esterification of the primery product gave the monoester (2) , R 1 = R 2 = H, R 3 = CH 2 CO 2 CH 3 , which can converted in only two steps into 9‐dexoy‐ε‐rhodomycinone (3) .