title: Medium-Sized Cyclic Ethers via Stevens [1,2]-Shift of Mixed Monothioacetal-Derived Sulfonium Ylides: Application to Formal Synthesis of (+)-Laurencin.
abstract: A novel approach to medium-sized cyclic ethers was devised using a Stevens [1,2]-shift of a sulfonium ylide derived from a readily accessible six-membered mixed-monothioacetal precursor. The concise and efficient transformation offers a surprising degree of chirality transfer with observed retention of stereochemical configuration on the anomeric migrating carbon and has been applied as the key step in an enantioselective formal synthesis of (+)-laurencin.
authors.affiliation: Department of Chemistry, University of Alberta , E3-43 Gunning-Lemieux Chemistry Center, Edmonton, AB T6G 2G2, Canada.
authors.forename: Rongrong
authors.initials: R
authors.lastname: Lin
authors.affiliation: Department of Chemistry, University of Alberta , E3-43 Gunning-Lemieux Chemistry Center, Edmonton, AB T6G 2G2, Canada.
authors.forename: Liya
authors.initials: L
authors.lastname: Cao
authors.affiliation: Department of Chemistry, University of Alberta , E3-43 Gunning-Lemieux Chemistry Center, Edmonton, AB T6G 2G2, Canada.
authors.forename: F G
authors.identifier: 0000-0001-7419-2314
authors.initials: FG
authors.lastname: West