“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

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.