Synthesis of (-)-pericosine B, the antipode of the cytotoxic marine natural product.
The stereoselective synthesis of (-)-pericosine B, which is the antipode of the cytotoxic metabolite of the fungus Periconia byssoides OUPS-N133 separated from the sea hare, was accomplished in 9 steps in 12% total yield from (-)-quinic acid, together with the synthesis of its epimer. Every crucial step of this total synthesis, including ring opening of a beta-epoxide and NaBH4 reduction of an unstable beta,gamma-unsaturated enone, proceeded with excellent stereoselectivity.
Usami
Yoshihide
Y
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. usami@gly.oups.ac.jp
Suzuki
Kentaro
K
Mizuki
Koji
K
Ichikawa
Hayato
H
Arimoto
Masao
M
D001688:Biological Products / Q000138:chemical synthesis / Q000633:toxicity; D045744:Cell Line, Tumor; D006801:Humans; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000633:toxicity; D013237:Stereoisomerism
D001688:Biological Products; C496389:pericosine B; D012765:Shikimic Acid