96239-70-2Relevant academic research and scientific papers
FORMAL SYNTHESIS OF LAVENDAMYCIN METHYL ESTER: THE REGIOSELECTIVE SYNTHESIS TO THE BROMOQUINOLINEQUINONE SYSTEMS OF KEY INTERMEDIATE
Hibino, Satoshi,Okazaki, Miko,Ichikawa, Masataka,Sato, Kohichi,Ishizu, Takashi
, p. 261 - 264 (2007/10/02)
We achieved a formal synthesis of lavendamycin methyl ester as follows.The Pictet-Spengler reaction of 8-benzyloxyquinolin-2-aldehyde 4 with β-methyltryptophan ethyl ester 5, gave pentacyclic β-carboline 7.Hydrogenolysis of benzyl ether 7 and bromination of 8-hydroxyquinoline 8 afforded 5,7-dibromo-8-hydroxyquinoline 11.Oxidation of bromophenol 11 by cerium ammonium nitrate proceeded regioselectively to the desired p-quinone system 13.On the other hand, the ethyl ester 8 was converted into its methyl ester 9 and led to the methyl ester of bromoquinolinequinone 14 regioselectively in the same way, that is, Kende's intermediate.
