title: Chiral version of the Burgess reagent and its reactions with oxiranes: application to the formal enantiodivergent synthesis of balanol.
abstract: An efficient formal synthesis of a (-)-balanol intermediate ( 25a) from cyclohexadiene oxide was accomplished in eight steps. An asymmetric version of the Burgess reagent allows for an enantiodivergent approach to both enantiomers of balanol from a racemic starting material.
authors.affiliation: Department of Chemistry, Brock University, Ontario, Canada.
authors.forename: Bradford
authors.initials: B
authors.lastname: Sullivan
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Gilmet
authors.forename: Hannes
authors.initials: H
authors.lastname: Leisch
authors.forename: Tomas
authors.initials: T
authors.lastname: Hudlicky
mesh_terms: D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D053138:Cyclohexenes / Q000737:chemistry*; D005027:Ethylene Oxide / Q000737:chemistry*; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001381:Azepines; D053138:Cyclohexenes; D062385:Hydroxybenzoates; D007202:Indicators and Reagents; C048401:1,4-cyclohexadiene; C015405:ophiocordin; D005027:Ethylene Oxide