title: γ-Substituted butanolides from cyclopropane hemimalonates: an expedient synthesis of natural (R)-dodecan-4-olide.
abstract: Exploration into the reactivity of donor-acceptor cyclopropane hemimalonates has led to the facile synthesis of γ-substituted butanolides. Under microwave irradiation, cyclopropane hemimalonates undergo rapid conversion to butanolides in the presence of inorganic salts with an unprecedented retention of stereochemistry. This unique process has been applied to the total synthesis of the naturally occurring (R)-dodecan-4-olide.
authors.affiliation: Department of Chemistry, The University of Western Ontario , London, Ontario, Canada N6A 5B7.
authors.forename: Huck K
authors.initials: HK
authors.lastname: Grover
authors.forename: Michael R
authors.initials: MR
authors.lastname: Emmett
authors.forename: Michael A
authors.initials: MA
authors.lastname: Kerr
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008314:Malonates / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C586610:(R)-dodecan-4-olide; D001688:Biological Products; D003521:Cyclopropanes; D007783:Lactones; D008314:Malonates; C030797:cyclopropane; D015107:4-Butyrolactone