"Endo" and "exo" bicyclo[4.2.0]-octadiene isomers from the electrocyclization of fully substituted tetraene models for SNF 4435C and D. control of stereochemistry by choice of a functionalized substituent.
[reaction: see text] A tandem electrocyclic closure, perceived as the key step in a biomimetic approach to SNF 4435C and D, was tested with 1,1,8-trisubstituted tetraene substrates. The ratio of endo:exo products could be controlled by the choice of the RZ substituent at C-1. On the basis of these results, a short stereoselective route to an advanced SNF 4435 intermediate was devised.
Parker
Kathlyn A
KA
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York, 11794-3400, USA. kparker@notes.cc.sunysb.edu
Lim
Yeon-Hee
YH
D003500:Cyclization; D004583:Electrons; D007536:Isomerism; D008968:Molecular Conformation; D009574:Nitro Compounds / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism
D009574:Nitro Compounds; D011753:Pyrones; C435067:SNF 4435C; C435066:SNF 4435D