79562-60-0Relevant academic research and scientific papers
Total Synthesis of a Mitosene
Rebek, Julius,Shaber, Steven H.,Shue, Youe-Kong,Gehret, Jean-Claude,Zimmerman, Stephen
, p. 5164 - 5174 (2007/10/02)
The total synthesis of a mitosene (a chemical degradation product of mitomycin C) is described.The synthesis begins with hydroxyproline and uses a Huisgen pyrrole synthesis to form a pyrrolizidine system.The carbocyclic ring is made through Dieckmann cycl
THE TOTAL SYNTHESIS OF A MITOSENE
Rebek, J.,Shaber, S.H.
, p. 1173 - 1177 (2007/10/02)
The conversion of L-hydroxyproline to a mitosene (degradation product of a mitomycin) is described.The synthesis involves 19 steps and the key stereochemical feature arises from an unusual cis opening of an epoxide.The synthetic product, 1-methoxy-2,7-diamino-mitosene is shown to be identical with the trans isomer obtained from acid-catalyzed methanolysis of mitomycin C.
