Enantioselective total synthesis of (+)-tricycloclavulone.
The first total synthesis of (+)-tricycloclavulone having a unique tricyclo[5,3,0,01,4]decane skeleton and six chiral centers was achieved in a highly stereoselective manner. It includes a catalytic enantioselective [2+2]-cycloaddition reaction using novel chiral copper catalyst, extremely effecting an intramolecular ester transfer reaction, and asymmetric reduction of the carbonyl group on the alpha-chain using Noyori's chiral ruthenium catalyst.
Ito
Hisanaka
H
School of Life Science, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan. itohisa@ls.toyaku.ac.jp
Hasegawa
Mineki
M
Takenaka
Yosuke
Y
Kobayashi
Tatsuya
T
Iguchi
Kazuo
K
D011453:Prostaglandins / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011453:Prostaglandins; C463699:tricycloclavulone