M. Nowakowski et Hmr. Hoffmann, SYNTHESIS OF BRIDGED 9-MEMBERED RING ETHERS - STUDIES DIRECTED TOWARDS THE SYNTHESIS OF EUNICELLIN-BASED MARINE DITERPENES, Tetrahedron, 53(12), 1997, pp. 4331-4338
A concise annulation-fragmentation strategy has been elaborated for th
e construction of the bridged nine-membered ring ether moiety of the e
unicelline diterpenes. Key steps are a SmI2-induced Barbier cyclizatio
n and an oxidative ring fission using cerium(IV) ammonium nitrate (CAN
). (C) 1997 Elsevier Science Ltd.