Intermolecular radical reaction of O,Se-acetals generated via seleno-Pummerer rearrangement.
A new general protocol for the synthesis of O,Se-acetals using the seleno-Pummerer reaction has been developed, and their radical-based two- and three-component coupling reactions were studied. The three-component coupling employed the O,Se-acetal, cyclopentenone, and an allylstannane derivative, and enabled stereoselective installations of α-acyloxy alkyl and functionalized allyl groups to generate the 2,3-trans-disubstituted cyclopentanone in a single operation. The obtained highly functionalized structure was used as an intermediate for facile assembly of the zedoarondiol carboskeleton.
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Tokyo 113-0033, Japan.
Daisuke
D
Urabe
Hiroki
H
Yamaguchi
Ayumi
A
Someya
Masayuki
M
Inoue
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D016566:Organoselenium Compounds / Q000737:chemistry*; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000080:Acetals; D007659:Ketones; D016566:Organoselenium Compounds; D009947:Organotin Compounds