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

It is observed that mesylate 1 on exposure to Li(Ot-Bu)(3)AlH in reflu xing 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 --> 6), has been used as the key to the total synt hesis of furanether B (4), a naturally occurring lactarane sesquiterpe ne, with the readily available ketone 8 as the starting material. Comp letion of the synthesis of the natural product is accomplished by an a nnulation method based on a Pummerer-induced cyclization reaction.