title: Asymmetric synthesis of seven-membered carbocyclic rings via a sequential oxyanionic 5-exo-dig cyclization/claisen rearrangement process. Total synthesis of (-)-frondosin B.
abstract: Appropriately substituted nonracemic allyl alcohols, readily prepared from the corresponding enones by application of the CBS methodology, were converted to optically active cycloheptenone derivatives with almost complete transfer of chirality via an efficient "one-pot", cycloisomerization/Claisen rearrangement process. This methodology was directly applied to the expedient total synthesis of (-)-frondosin B.
authors.affiliation: Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, USA. tVoVa@conncoll.edu
authors.forename: Timo V
authors.initials: TV
authors.lastname: Ovaska
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Sullivan
authors.forename: Sami I
authors.initials: SI
authors.lastname: Ovaska
authors.forename: Jacob B
authors.initials: JB
authors.lastname: Winegrad
authors.forename: Justin D
authors.initials: JD
authors.lastname: Fair
mesh_terms: D000838:Anions / Q000737:chemistry*; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D000838:Anions; D006576:Heterocyclic Compounds, 4 or More Rings; C421322:frondosin B