Tetraquinanes via [4 + 4] photocycloaddition/transannular ring closure.
Intramolecular [4 + 4] photocycloaddition of a furan and a cyclopentane-annulated 2-pyridone yields a cyclooctadiene product with four new stereogenic centers. Transannular ring closure produces the 5-5-5-5 fused ring system of the crinipellins, including three contiguous quaternary carbons, with the correct absolute stereochemistry derived from (-)-carvone.
Chen
Peiling
P
Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, USA.
Carroll
Patrick J
PJ
Sieburth
Scott McN
SM