title: A series of two oxidation reactions of ortho-alkenylbenzamide with hypervalent iodine(III): a concise entry into (3R,4R)-4-hydroxymellein and (3R,4R)-4-hydroxy-6-methoxymellein.
abstract: A sequence of oxidation reactions of alkenamides with hypervalent iodine is described. Oxidation of ortho-alkenylbenzamide substrates selectively gave isochroman-1-imine products. The products underwent further oxidation in the presence of a Pd salt catalyst leading to regioselective C-H acetoxylation at the 8-position. A series of oxidations was applied to the crucial steps of asymmetric synthesis of 4-hydroxymellein derivatives.
authors.affiliation: Graduate School of Material Science, University of Hyogo , Kohto, Kamigori, Hyogo 678-1297, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Takesue
authors.forename: Morifumi
authors.initials: M
authors.lastname: Fujita
authors.forename: Takashi
authors.initials: T
authors.lastname: Sugimura
authors.forename: Hiroki
authors.initials: H
authors.lastname: Akutsu