Total synthesis and determination of the absolute configuration of (+)-omaezakianol.
The proof of the pudding: The first asymmetric total synthesis of the marine tetracyclic oxasqualenoid (+)-omaezakianol features a convergent olefin cross-metathesis between a monotetrahydrofuran fragment and a triepoxy alkene, and cascade oxacyclizations of a triepoxy alcohol to form the right-hand three ether rings. The total synthesis proved the absolute configuration of (+)-omaezakianol to be that shown.
Morimoto
Yoshiki
Y
Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan. morimoto@sci.osaka-cu.ac.jp
Okita
Tatsuya
T
Kambara
Hitomi
H
D008968:Molecular Conformation; D013185:Squalene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D013729:Terpenes; C540153:omaezakianol; D013185:Squalene