1964-58-5

Upstream product

• 99394-31-7 (2R,3S,4R)-3,4-dihydroxy-2-(p-methoxybenzyl)pyrrolidine hydrochloride 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 824-94-2 p-methoxybenzyl chloride 
• 87796-29-0 5-deoxy-2,3-O-isopropylidene-5-(p-methoxyphenyl)-β-L-ribofuranose 
• 883236-75-7 (1S,2R,5R)-2-(4-Methoxy-benzyl)-3-(toluene-4-sulfonyl)-6-oxa-3-aza-bicyclo[3.1.0]hexane 
• 87796-36-9 (E,Z)-5-deoxy-2,3-O-isopropylidene-5-(p-methoxyphenyl)-L-ribose oxime 
• 87859-50-5 (2R,3S,4R)-3,4-isopropylidenedioxy-2-(p-methoxybenzyl)-pyrrolidine 
• 87796-40-5 5-deoxy-2,3-O-isopropylidene-4-O-methylsulphonyl-5-(p-methoxyphenyl)-L-ribononitrile 
• 87796-27-8 1-deoxy-3,4-O-isopropylidene-1-(p-methoxyphenyl)-D-allitol 
• 38769-92-5 4-methoxybenzylmagnesium chloride 
• 883236-74-6 (2S,3S)-3-Amino-1-(4-methoxy-phenyl)-pent-4-en-2-ol 

Downstream Products

• 87796-46-1 (2R,3S,4S)-4-allyloxy-3-hydroxy-2-(p-methoxybenzyl)-pyrrolidine 
• 1964-55-2 2t-(4-methoxy-benzyl)-4t-morpholin-4-yl-pyrrolidin-3r-ol 
• 933992-79-1 (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine 
• 87796-48-3 (2R,3S,4S)-3-acetoxy-4-allyloxy-1-benzyl-2-(p-methoxybenzyl)pyrrolidine 
• 22862-76-6 (-)-anisomycin 

Relevant academic research and scientific papers

Microwave-assisted rearrangement of vinylaziridines to 3-pyrrolines: Formal synthesis of (-)-anisomycin

An efficient microwave-assisted rearrangement of activated vinylaziridines to 3-pyrrolines is described. The rearrangement proceeds in good to excellent yields and is mediated by NaI or LiI in MeCN at elevated temperatures. The synthetic utility of this r

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

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) , 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 .