Facile and efficient synthesis of naturally occurring carbasugars (+)-pericosines A and C.
An efficient synthesis of antitumor marine natural product (+)-pericosine A was achieved from (-)-quinic acid in 11.7% overall yield, which is 20 times better than our previously reported synthesis. The crucial steps of this synthesis include the regio- and stereoselective bromohydrination of an unstable diene and the ring opening of an epoxide. This synthetic route was applicable to a synthesis of (+)-pericosine C and also to a synthesis of (-)-pericosine C.
Usami
Yoshihide
Y
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. usami@gly.oups.ac.jp
Ohsugi
Marie
M
Mizuki
Koji
K
Ichikawa
Hayato
H
Arimoto
Masao
M
D054329:Carbasugars / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D054329:Carbasugars; D004852:Epoxy Compounds; D010756:Phosphoric Acids; C523077:methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate; C544052:pericosine C; D012765:Shikimic Acid; D008982:Molybdenum; C003125:phosphomolybdic acid