Construction of eight-membered ether rings by olefin geometry-dependent internal alkylation: first asymmetric total syntheses of (+)-3-(E)- and (+)-3-(Z)-pinnatifidenyne.
The first and highly stereoselective asymmetric total syntheses of eight-membered ring ether marine natural products (+)-3-(E)-pinnatifidenyne and (+)-3-(Z)-pinnatifidenyne have been accomplished. Notable features of our syntheses include a novel and efficient construction of oxocene 5 by a highly stereo- and regioselective internal alkylation and direct ketone synthesis of ketone 16 from the alpha-alkyloxy amide moiety in oxocene 5.
Kim
Hyoungsu
H
Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, San 56-1, Shinrim-Dong, Kwanak-Ku, Seoul 151-742, Korea.
Choi
Won Jun
WJ
Jung
Jaeyoon
J
Kim
Sanghee
S
Kim
Deukjoon
D
D000478:Alkylation; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D000461:Rhodophyta / Q000737:chemistry; D013237:Stereoisomerism
C480362:3-pinnatifidenyne; D004988:Ethers, Cyclic