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A New Synthesis of (-)-Anisomycin and its Demethoxy analogue from D-Ribose

DOI: 10.1039/P19850001463

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1463 - 1470 (1985)

Update date:2022-08-05

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Authors:

Buchanan, J. GrantBuchanan, J. Grant

MacLean, Keith A.MacLean, Keith A.

Wightman, Richard H.Wightman, Richard H.

Paulsen, HansPaulsen, Hans

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Article abstract of DOI:10.1039/P19850001463

2,3-O-Isopropylidene-D-ribose (7) reacted with p-methoxybenzylmagnesium chloride in tetrahydrofuran to give the D-allotriol (6a) (77percent).Periodate oxidation of compound (6a) followed by reaction with hydroxylamine hydrochloride in pyridine gave (E,Z)-5-deoxy-2,3-O-isopropylidene-5-(p-methoxyphenyl)-L-ribose oxime (18a) which was converted into the nitrile methanesulphonate (19a) with methanesulphonyl chloride in pyridine.Reduction of the nitrile (19a) with lithium aluminium hydride gave (2R,3S,4R)-3,4-isopropylidenedioxy-2-(p-methoxybenzyl)pyrrolidine (2a) <45percent from (6a)>, which was converted into the epoxide (24a) (68percent) via the bromo acetates (28a) and (29a).Regioselective opening of the epoxide ring in compound (24a) with acidic allyl alcohol gave the allyl ether (30a) (63percent) which was converted into the N-benzyl 3-acetoxy compound (31a) (77percent).Removal of the allyl and benzyl groups, by treatment with palladium-charcoal under acidic conditions followed by hydrogenolysis, gave (-)-anisomycin (1a (86percent). A similar series of reactions afforded demethoxyanisomycin (1b) which showed antibiotic activity against Trichomonas vaginalis .

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Product name:3,4-di-O-acetyl-1-deoxy-2,5-di-O-methylsulphonyl-1-phenyl-D-ribitol

Cas No:99284-53-4

99284-53-4

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