First total synthesis of antitumor natural product (+)- and (-)-pericosine A: determination of absolute stereo structure.
The first total synthesis of (+)- and (-)-pericosine A has been achieved, enabling the revision and determination of the absolute configuration of this antitumor natural product as methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate. Every step of this total synthesis proceeded well with excellent stereoselectivity. Structures of the intermediates in crucial steps were confirmed by detailed 2D NMR analysis.
Usami
Yoshihide
Y
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. usami@gly.oups.ac.jp
Takaoka
Isao
I
Ichikawa
Hayato
H
Horibe
Yusuke
Y
Tomiyama
Syunsuke
S
Ohtsuka
Misako
M
Imanishi
Yumi
Y
Arimoto
Masao
M
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D002264:Carboxylic Acids; C523077:methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate; D012765:Shikimic Acid