Synthesis of the Anthraquinone Framework of Dynemicin A | Zendy

Nicolaou K. C. | Zendy; Gross Jonathan L. | Zendy; Kerr Michael A. | Zendy; Lemus Robert H. | Zendy; Ikeda Kiyoshi | Zendy; Ohe Kouichi | Zendy

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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.

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