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Synthesis of the Anthraquinone Framework of Dynemicin A
Author(s) -
Nicolaou K. C.,
Gross Jonathan L.,
Kerr Michael A.,
Lemus Robert H.,
Ikeda Kiyoshi,
Ohe Kouichi
Publication year - 1994
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.199407811
Subject(s) - anthraquinone , ketone , total synthesis , moiety , quinone , quinoline , electrophile , chemistry , benzophenone , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
Within reach appears to be the total synthesis of dynemicin A now that after the preparation of the endiyne moiety, the synthesis of the pentacyclic anthraquinone skeleton has been achieved. Starting from 1 , the key steps of the reaction sequence are two ortho metalations at quinoline which furnish the ketone 2 after quenching with the appropriate electrophile, cyclization, and oxidation. The ketone is probably a suitable precursor for the total synthesis of this cystostatic and antibiotic agent.