title: Diels-Alder reaction of maldoxin with an isopropenylallene.
abstract: The Diels-Alder reaction of maldoxin with an isopropenylallene at 60-75 °C afforded an adduct closely related to chloropestolide A (24%) and a second adduct (0-11%) that underwent an ene reaction to generate the chloropupukeanolide D (11-22%) skeleton. The Diels-Alder reaction occurred with good selectively (>5:1) from a single face of maldoxin under much milder conditions than previously reported for the analogous dimethoxycyclohexadienone. Furthermore, the ene reaction took place under mild conditions whereas the analogous Diels-Alder adduct from the dimethoxycyclohexadienone did not undergo an ene reaction.
authors.affiliation: Department of Chemistry MS 015,Brandeis University, Waltham, Massachusetts, 02454-9110, USA.
authors.forename: Min
authors.initials: M
authors.lastname: Yu
authors.forename: Barry B
authors.initials: BB
authors.lastname: Snider