136520-27-9

Basic information

• Product Name: (+/-)-4-epi-Acetomycin
• CAS NO: 136520-27-9
• Molecular Weight: 214.218
• Mol File: 136520-27-9.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-4-epi-Acetomycin(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-4-epi-Acetomycin(136520-27-9)
• EPA Substance Registry System: (+/-)-4-epi-Acetomycin(136520-27-9)

Safety Data

• Hazardous Substances Data: 136520-27-9(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 138648-06-3 2-Isopropenyl-2,3-dimethyl-pent-4-enoic acid 
• 138648-02-9 2-Acetyl-2,3-dimethyl-pent-4-enoic acid 
• 103560-90-3 Acetic acid (2S,3R,4R)-4-(1-hydroxy-ethyl)-3,4-dimethyl-5-oxo-tetrahydro-furan-2-yl ester 
• 103560-90-3 Acetic acid (2R,3R,4R)-4-(1-hydroxy-ethyl)-3,4-dimethyl-5-oxo-tetrahydro-furan-2-yl ester 
• 131404-94-9 4-Methyl-5-acetoxy-2-furanone 
• 40834-42-2 5-hydroxy-4-methyl-5H-furan-2-one 
• 74-88-4 methyl iodide 
• 74-83-9 methyl bromide 
• 136409-66-0 Acetic acid (2S,3R,4R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dimethyl-5-oxo-tetrahydro-furan-2-yl ester 
• 136409-66-0 Acetic acid (2R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dimethyl-5-oxo-tetrahydro-furan-2-yl ester 
• 136409-61-5 (3S,4R)-4-(4-Methoxy-benzyloxymethyl)-3,4-dimethyl-dihydro-furan-2-one 
• 136409-64-8 tert-Butyl-[(2S,3S)-2-(4-methoxy-benzyloxymethyl)-2,3-dimethyl-pent-4-enyloxy]-dimethyl-silane 

Relevant articles and documents

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.

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

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.