Abstract
Reaction of levoglucosenone (1,6-anhydro-3,4-dideoxy-β- d- glycero-hex-3-enopyranos-2-ulose) with o-xylylene generated from o-bis(bromomethyl)benzene by treatment with zinc under ultrasonic irradiation gave 53% of the exo-adduct (1 S,3 R,4a R,10a S)-3,11-anhydro-3-hydroxy-1-hydroxymethyl-4-oxo-3,4,5,10-tetrahydronaphtho[2,3- c]pyran ( 11) together with small proportions of the tertiary alcohols (1 S,3 R,4a R,10a S)-3,11-anhydro-3,4-dihydroxy-1-hydroxymethyl-4- C-( o-methylbenzyl)-3,4,5,10-tetrahydronaphtho[2,3- c]pyran ( 12) and 1,6-anhydro-3,4-dideoxy-2- C-( o-methylbenzyl)-β- d- erythro,threo-hex-3-enopyranose ( 13). Reduction of 11 afforded the epimeric alcohols 14 and 15 which, on conversion into their xanthates 18 and 19 and treatment with tributyltin hydride, gave the deoxy compound (1 S,3 R,4a R,10a S)-3,11-anhydro-3-hydroxy-1-hydroxymethyl-3,4,5,10-tetra-hydronaphtho[2,3- c]pyran ( 20), which affords potential access to the pyranonaphthoquinones.
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