title: Unique reactivity of anti- and syn-acetoxypyranones en route to oxidopyrylium intermediates leading to a cascade process.
abstract: Unique reactivity of anti- and syn-acetoxypyranones was observed in oxidopyrylium-alkene [5 + 2] cycloadditions. The subtle interplay between the corresponding acetoxypyranone conformation and steric bulk of tertiary amine bases causes syn-acetoxypyranones to undergo [5 + 2] cycloaddition appreciably faster than anti-acetoxypyranones. Additionally, the efficiency of a cascade process that afforded a novel tetracyclic lactol was determined to be dependent on the relative stereochemistry of each diastereomer, the amine base utilized, and the addition of water.
authors.affiliation: Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, USA.
authors.forename: Erica L
authors.initials: EL
authors.lastname: Woodall
authors.forename: Justin A
authors.initials: JA
authors.lastname: Simanis
authors.forename: Christopher G
authors.initials: CG
authors.lastname: Hamaker
authors.forename: John R
authors.initials: JR
authors.lastname: Goodell
authors.forename: T Andrew
authors.initials: TA
authors.lastname: Mitchell