Abstract
Regioselective introduction of a benzoxy group, in the benzylic position of the β-benzyl-γ-butyrolactone (R)-(+)- 8, was achieved by tretment with NBS followed with benzyl alcohol. α-Alkylation of the lithium enolate of the resulting intermediate 11, with O -benzylvanillyl bromide 5, gave the trans disubstituted lactone 13. Catalytic hydrogenolysis (PdC) of 13 selectively split the aryl benzyl ether linkage, thus giving the compound 14. Intramolecular Friedel-Crafts cyclisation of the latter, using the benzoxy group as the leaving group, was induced with BF 3. Et 2O and afforded high yields of (−)-α-conidendrin 2.
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