合成路线1

Treatment of 3-bromobenzyl bromide (I) with sodium methoxide gives 1-bromo-3-(methoxymethyl)benzene (II). After conversion of aryl bromide (II) into the corresponding Grignard reagent (III), addition to epoxide (IV) in the presence of CuI affords the chiral alcohol (V). Removal of the O-trityl protecting group of (V) under acidic conditions provides diol (VI), which is selectively acylated at the primary hydroxyl group by means of acetyl chloride and 2,4,6-collidine to produce the mono-acetate (VII). After protection of the secondary hydroxyl group of (VII) as the tetrahydropyranyl ether (VIII), alkaline hydrolysis of the acetate ester group leads to the primary alcohol (IX). Subsequent Swern oxidation of alcohol (IX) provides aldehyde (X). Condensation of aldehyde (X) with tetrabromomethane in the presence of triphenylphosphine furnishes the gem-dibromoolefin (XI). This is then converted to the terminal alkyne (XII) by treatment with butyllithium in cold THF.