title: The dihydrofuran template approach to furofuran synthesis.
abstract: Flash vacuum pyrrolysis of vinyl epoxides provides cis-dihydrofuran carboxylic esters in good yields and diastereoselectivities, which, on base-promoted epimerisation afford the complementary trans series. The compounds provide a viable template for a Lewis acid promoted cyclisation to provide the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane core found in the furofuran series of natural lignans. This strategy is stereodivergent and can be controlled to provide the exo-exo, exo-endo or endo-endo stereochemistries. The approach has been exemplified in syntheses of the sesamyl furofurans (+/-)-epiasarinin and (+/-)-asarinin.
authors.affiliation: Sanofi-Aventis Pharma Inc, Bridgewater, New Jersey 08807, USA.
authors.forename: David J
authors.initials: DJ
authors.lastname: Aldous
authors.forename: Andrei S
authors.initials: AS
authors.lastname: Batsanov
authors.forename: Dmitrii S
authors.initials: DS
authors.lastname: Yufit
authors.forename: Anne J
authors.initials: AJ
authors.lastname: Dalençon
authors.forename: William M
authors.initials: WM
authors.lastname: Dutton
authors.forename: Patrick G
authors.initials: PG
authors.lastname: Steel
mesh_terms: D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D013058:Mass Spectrometry
chemical_list: D005663:Furans