title: Cyclopropane compatibility with oxidative carbocation formation: total synthesis of clavosolide A.
abstract: Cyclopropane-substituted allylic ethers react with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form oxocarbenium ions with no competitive ring cleavage. This reaction can be used for the preparation of cyclopropane-substituted tetrahydropyrans. The protocol was used as a key step in the total synthesis of the sponge-derived macrolide clavosolide A.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
authors.forename: GuangRong
authors.initials: G
authors.lastname: Peh
authors.forename: Paul E
authors.initials: PE
authors.lastname: Floreancig
mesh_terms: D000818:Animals; D016227:Benzoquinones / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry
chemical_list: D016227:Benzoquinones; D003521:Cyclopropanes; D018942:Macrolides; C455699:clavosolide A; C004532:quinone; C030797:cyclopropane