Synthesis of the bicyclo[7.3.0]dodecadiyne core of the maduropeptin chromophore.
Maduropeptin, an extremely potent antitumor agent, consists of a 1:1 complex of a carrier protein and a chromophore. We report herein a general and efficient route for the synthesis of the highly strained bicyclo[7.3.0]dodecadiyne core of the chromophore. The key feature of the synthetic strategy is the use of two Sonogashira coupling reactions in a stepwise manner to construct the conjugated dienyne substructure of the fused-ring system, including the Z alkene at C4,C13.
Iso
Kentaro
K
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Inoue
Masayuki
M
Kato
Nobuki
N
Hirama
Masahiro
M
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D053281:Enediynes / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*
D001643:Bridged Bicyclo Compounds; D053281:Enediynes; D010455:Peptides