510-18-9

Usage

Uses

Acetomycin is an anti-biotic, anti-fungal, anti-protozoal, and anti-bacterial agent.

InChI:InChI=1/C10H14O5/c1-5-8(14-7(3)12)15-9(13)10(5,4)6(2)11/h5,8H,1-4H3/t5-,8-,10+/m1/s1

Upstream product

• 208172-57-0 (3R)(4S)(5R)-5-acetoxy-3-acetyl-3-(1,3-dithianyl)-4-methyl-dihydro-2(3H)-furanone 
• 635317-44-1 (3S,4S,5S)-5-Hydroxy-3,4-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)-dihydro-furan-2-one 
• 635317-41-8 (E)-(2S,3R)-2-Acetyl-2,3-dimethyl-5-phenyl-pent-4-enoic acid methyl ester 
• 180063-09-6 (-)-5-(R)-acetoxy-4-methyl-2(5H)-furanone 
• 53651-72-2 diethyl allylmethylmalonate 
• 136409-63-7 2,2-Dimethyl-propionic acid (2R,3S)-4-hydroxy-2-(4-methoxy-benzyloxymethyl)-2,3-dimethyl-butyl ester 
• 136409-62-6 2,2-Dimethyl-propionic acid (2R,3R)-3-hydroxymethyl-4-(4-methoxy-benzyloxy)-2,3-dimethyl-butyl ester 
• 136409-61-5 (3S,4R)-4-(4-Methoxy-benzyloxymethyl)-3,4-dimethyl-dihydro-furan-2-one 
• 74-83-9 methyl bromide 
• 40834-42-2 5-hydroxy-4-methyl-5H-furan-2-one 
• 119274-24-7 (2R,3R,4S,5S)-4-<(1S)-1-(ethoxycarbonyl)ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran 
• 141585-50-4 (3aR,5S,6R,6aR)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde 
• 141585-51-5 (3aR,5S,6R,6aR)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5,6-dicarbaldehyde 
• 119274-27-0 (2R,3R,4S,5S)-4-<(1S)-1-<(benzyloxy)methyl>ethyl>-5-<(1R)-1,2-dihydroxyethyl>-2,3-(isopropylidenedioxy)-4-vinyltetrahydrofuran 

Downstream Products

• 1121-05-7 2,3-dimethylcyclopent-2-enone 

Relevant academic research and scientific papers

Asymmetric synthesis of acetomycin

The synthesis of (-)-acetomycin 1, a highly functionalized γ-lactone with antitumor activity, was achieved in five steps with nearly complete enantioselectivity. The key step was realized by a large scale lipase R catalyzed esterification of 5-hydroxy-4-methyl-2(5H)-furanone 2 providing (- )-(5R)-5-acetoxy-4-methyl-2(5H)-furanone 3 with an e.e. of 99%.

Construction of Consecutive Chiral Non-Racemic Quaternary and Tertiary Carbon Centers: A Short Synthetic Route to (-)-Acetomycin

Regio- and diastereoselective nucleophilic substitution of 2-methylacetoacetate with a chiral non-racemic π-allyl Pd complex creates consecutive chiral non-racemic quaternary and tertiary carbon centers. σ-Bond formation between the reface of the π-allyl Pd complex and the re-face of the enol acetoacetate was controlled by the o-(diphenylphosphanyl)-arylcarboxylic acid ligand selectively. (-)-Acetomycin was synthesized in seven steps using this key approach. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Total synthesis of (+/-)-acetomycin and design of esterase-resistant analogs.

The synthesis of acetomycin and related analogs was investigated. Acetomycin was synthesized from diethyl allyl(methyl)malonate in 6.5% yield over 18 steps. The total number of steps was improved compared to our previous synthesis; i.e., four steps shorte

Unexpected Contrasteric Alkylation Leading to a Model for Five-Membered Ring Enolate Alkylation: Short Stereoselective Synthesis of (+/-)-Acetomycin

It is well established that the alkylation of cyclic enolates 1 bearing an asymmetric center at the β-position should provide mainly lactones 2 where the electrophile (E(+)) ends up trans to the β-substituent (R2).Our interest in such processes lies in the fact that according to this principle, alkylation of 1a with methyl iodide should provide direct access to (+/-)-acetomycin (2a).However, this reaction unexpectedly afforded the contrasteric alkylation product 3a ((+/-)-3-epi-acetomycin) with high diastereoselectivity.To elucidate this observation, alkylation studies have been carried out on various enolates 1.As normally expected, when R2 and R3 are alkyl groups, only product 2 is obtained.On the other hand, when R3 is an acetoxy group or an alkoxy group and methyl iodide is used as electrophile, the contrasteric products 3 are predominant.With sterically more demanding electrophiles, the "normal" alkylation products 2 are obtained in moderate to extremely high selectivity.Thus, the use of 1,3-dithienium tetrafluoroborate, a bulky methyl equivalent, allowed us to complete a stereoselective syntheses of (+/-)-acetomycin.These results led to the elaboration of a model for five-membered ring enolate alkylation based on steric and stereoelectronic effects, as well as ring conformations.

A Selective Baeyer-Villiger Oxidation: A Total Synthesis of (-)-Acetomycin

A short, stereoselective synthesis of (-)-acetomycin (2) from L-threonine is reported.The final step in the synthesis is a selective Baeyer-Villiger oxidation that discriminates between two methyl ketones.

TOTAL SYNTHESIS OF (+/-)-ACETOMYCIN

A stereocontrolled total synthesis of (+/-)-Acetomycin (1) is described.The acyloxy group was successfully introduced from sterically hindered α-side onto the γ-butyrolactone ring.

Stereoselective synthesis of (±)-4-epi-acetomycin by the ester enolate carroll rearrangement

The synthesis of (+-)-4-epi-acetomycin has been completed by the steroselective ester enolate (Carroll rearrangement of (E)-2-butenyl 2-methylacetoacetate, followed by ozonolysis and acetylation. The synthesis of (+)- acetomycin and its three diastereomers by a related route is also described.

Total synthesis of (-)-acetomycin

Enantiospecific total synthesis of the rifled antibiotic (1) has been completed. The pentasubstituted tetrahydrofuran (3), efficiently obtained from D-glucose, was used as an enantiomerically pure starting material.