Formal total synthesis of neocarzinostatin chromophore.
[reaction: see text] An efficient route to the neocarzinostatin chromophore aglycon has been developed. The present strategy involves a stereoselective intramolecular acetylide-aldehyde cyclization to form the C5-C6 bond, followed by efficient installation of alpha-epoxide, naphthoate, and carbonate functionalities. The C8-C9-olefin was introduced by using the Martin sulfurane dehydration reaction to furnish the highly reactive aglycon.
Kobayashi
Shoji
S
Department of Chemistry, Graduate Schools of Science, Tohoku University, Sendai 980-8578, Japan. koba@c.s.osakafu-u.ac.jp
Hori
Makiko
M
Wang
Guang Xing
GX
Hirama
Masahiro
M
D053281:Enediynes; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D009353:Zinostatin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D053281:Enediynes; D007202:Indicators and Reagents; C032372:neocarzinostatin chromophore; D009353:Zinostatin