745809-48-7Relevant academic research and scientific papers
Syntheses of prekinamycin and a tetracyclic quinone from common synthetic intermediates
Kimura, Shingo,Kobayashi, Satoshi,Kumamoto, Takuya,Akagi, Aki,Sato, Naomi,Ishikawa, Tsutomu
, p. 578 - 591 (2011/06/18)
Towards total synthesis of a series of kinamycin and related antibiotics via common synthetic intermediates, total synthesis of prekinamycin was achieved via Suzuki coupling of naphthaleneboronic acid and bromobenzene derivative, intramolecular Friedel-Crafts reaction of 2-(naphthalen-2-yl)benzoic acid, and diazotization in ten steps from 3,5-dimethylphenol. Synthetic studies towards kinamycin antibiotics was also examined, and the tetracyclic quinone core for kinamycins was synthesized. Palladium-catalyzed site-selective hydroxylation of a benzoic acid derivative with the AB-D ring part was successfully applied to the selective D-ring functionalizations. Copyright
Studies on the synthesis of landomycin A. Synthesis of the originally assigned structure of the aglycone, landomycinone, and revision of structure
Roush, William R.,Neitz, R. Jeffrey
, p. 4906 - 4912 (2007/10/03)
The originally proposed structure (2) of landomycinone, the aglycone of landomycin A, has been synthesized and shown to be nonidentical to the naturally derived landomycin A aglycone. The synthesis of 2 features the Doetz benzannulation reaction of chromium carbene 5 and alkyne 6, and the intramolecular Michael-type cyclization reaction of the phenolic naphthoquinone 20. It is proposed that natural landomycinone possesses the alternative structure 3, but attempts to access this structure via the Michael-type cyclization of the isomeric phenolic naphthoquinone 38 have been unsuccessful.
