title: Base-Induced Rearrangement of Perhydronaphthalene-1,4-diol Monosulfonate Esters to 11-Oxatricyclo[5.3.1.0(2,6)]undecanes. Total Synthesis of Furanether B.
abstract: It is observed that mesylate 1 on exposure to Li(Ot-Bu)(3)AlH in refluxing toluene rearranges selectively to the 11-oxatricyclo[5.3.1.0(2,6)]undecane derivative 3. A similar rearrangement, leading to a bridged tricyclic ether (14 --> 5), has been used as the key to the total synthesis of furanether B (4), a naturally occurring lactarane sesquiterpene, with the readily available ketone 8 as the starting material. Completion of the synthesis of the natural product is accomplished by an annulation method based on a Pummerer-induced cyclization reaction.
authors.affiliation: Laboratory of Organic Chemistry, Agricultural University, Dreijenplein 8, 6703 HB Wageningen, The Netherlands.
authors.forename: Roel P. L.
authors.initials: RP
authors.lastname: Bell
authors.forename: Arkadij
authors.initials: A
authors.lastname: Sobolev
authors.forename: Joannes B. P. A.
authors.initials: JB
authors.lastname: Wijnberg
authors.forename: Aede
authors.initials: A
authors.lastname: de Groot