116589-07-2Relevant academic research and scientific papers
Synthesis of 9a-Deoxymitomycin Congeners
Naruta, Yoshinori,Nagai, Naoshi,Maruyama, Kazuhiro
, p. 1143 - 1148 (2007/10/02)
The protected mitosane (23) is prepared in stereospecific manner.The key reactions included in the synthetic scheme are (i) Lewis acid-mediated Claisen-type rearrangement of the penta-2,4-dienyl aryl ether (10) to the penta-2,4-dienylphenol (11), (ii) the regioselective incorporation of the alkoxymethyl group at the 1-position of the pentadienyl side-chain in the protected pentadienylhydroquinone (12), and (iii) the stereospecific copper-catalysed double cyclization of the azido(penta-2,4-dienyl)quinone (15) to the 3H-pyrroloindole-5,8-dione (16) in one step.Subsequent stereospecific introduction of the aziridine ring furnishes the target compound (23).
