Construction of Eight-Membered Ether Rings by Olefin
Geometry-Dependent Internal Alkylation: First Asymmetric
Total Syntheses of (+)-3-(E)- and (+)-3-(Z)-Pinnatifidenyne
posted on 2003-07-17, 00:00authored byHyoungsu Kim, Won Jun Choi, Jaeyoon Jung, Sanghee Kim, Deukjoon Kim
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 α-alkyloxy amide
moiety in oxocene 5.