Synthesis of chloroquinocin, a pyranonaphthoquinone antibiotic against Gram-positive bacteria

Tetrahedron Letters

Volumn 48, Issue 9, 2007, Pages 1545-1548

  Shimbashi, Akiko ^a   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Antibiotic; Chlorination; Chloroquinocin; Gram positive bacteria; Methicillin resistant Staphylococcus aureus; Pyranonaphthoquinone

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ANTIBIOTIC AGENT; CHLOROQUINOCIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; DRUG SYNTHESIS; GRAM POSITIVE BACTERIUM; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN;

METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

EID: 33846595262     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.020     Document Type: Article

References (14)

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13. In the synthesis of 1, this chlorination reaction was the crucial step for the construction of a chlorinated naphthoquinone. We have attempted the following approaches, in addition to the process (13-3). When naphthalene derivative I, synthesized from intermediate 5, was used as a precursor of chlorination, the desired chlorinated naphthalene II was not obtained, but a complicated mixture including the oxidized product III (Scheme 5). Moreover, in the case of pyranonaphthoquinone IV, a chlorine atom was induced the benzylic position to give the undesired compound VI. Therefore, it was concluded that the naphthoquinone as a precursor and NCS/MeOH conditions were essential factors to build the chlorinated naphthoquinone framework.
14. 6) 0.90 (t, 3H, J = 7.2 Hz), 1.42-1.47 (complex, 2H), 1.91 (complex, 2H), 5.53 (dd, 1H, J = 2.9, 9.2 Hz), 5.85 (s, 1H), 7.22 (s, 1H), and 12.67 (s, 1H).