Abstract
Reaction of 2,3-O-isopropylidene-D-ribose (8) with diallylzinc gave a triol, which on treatment with periodate was converted into 5,6,7-trideoxy-2,3-O-isopropylidene-L-ribo-hept-6-enofuranose (10)(86%). Reaction with hydroxylamine hydrochloride in pyridine gave an oxime (11), which was treated with methanesulphonyl chloride in pyridine to yield 5,6,7-trideoxy-2,3-O-isopropylidene-4-O-methylsulphonyl-L-ribo-hept-6-enononitrile (12)(87% overall). Reduction with lithium aluminium hydride and cyclisation followed by treatment with benzyl chloroformate gave (2R,3S,4R)-2-allyl-1-benzyloxycarbonyl-3,4-isopropylidenedioxypyrrolidine (14), which on oxidation and subsequent reaction with diazomethane yielded (2R,3S,4R)-methyl (1-benzyloxycarbonyl-3,4-isopropylidenedioxypyrrolidin-2-yl)acetate (15b)(35%).
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