Oudemansin A

Base Information

• Chemical Name: Oudemansin A
• CAS No.: 73341-71-6
• Molecular Formula: C17H22 O4
• Molecular Weight: 290.35418
• UNII: AF4T7P745Y
• DSSTox Substance ID: DTXSID401031462
• Nikkaji Number: J96.938I
• Wikipedia: Oudemansin_A
• Wikidata: Q16979497
• ChEMBL ID: CHEMBL1094279
• Mol file: 73341-71-6.mol

Synonyms:5-Hexenoic acid, 4-methoxy-2-(methoxymethylene)-3-methyl-6-phenyl-, methyl ester, (2E,3R*,4R*,5E)-(-)-;oudemansin;oudemansin B

Chemical Property of Oudemansin A

Chemical Property:

• Vapor Pressure: 5.97E-07mmHg at 25°C
• Boiling Point: 410.5°C at 760 mmHg
• Flash Point: 179.2°C
• PSA: 44.76000
• Density: 1.064g/cm³
• LogP: 3.05420
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 290.15180918
• Heavy Atom Count: 21
• Complexity: 367

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C=CC1=CC=CC=C1)OC)C(=COC)C(=O)OC
• Isomeric SMILES: C[C@H]([C@H](/C=C/C1=CC=CC=C1)OC)/C(=C\OC)/C(=O)OC

Technology Process of Oudemansin A

There total 68 articles about Oudemansin A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester (90664-08-7) + dimethyl sulfate (77-78-1) → (-)-oudemanisin A (73341-71-6)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tetasy.2017.06.002

Reference yield:

(E)-(3R*,4S*)-4-methoxy-3-methyl-6-phenylhex-5-enol (88088-55-5,109864-29-1,109864-30-4,109864-31-5) → oudemansin A (73341-71-6,82444-24-4,82444-25-5,88644-09-1,90695-49-1,90695-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 8 N Jones reagent / acetone / 2 h

2: 1.) t-BuLi, 2.) K₂CO₃ / 2.) acetone

With jones reagent; tert.-butyl lithium; potassium carbonate; In acetone;

DOI:10.1021/jo00228a028

Reference yield:

(E)-(3S*,4R*)-3-methoxy-4-methyl-1-phenylhexa-1,5-diene (88088-54-4,106315-62-2,109864-19-9,109864-32-6) → oudemansin A (73341-71-6,82444-24-4,82444-25-5,88644-09-1,90695-49-1,90695-50-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 9-BBN, 2.) 15percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, from 0 deg C to RT, overnight, 2.) THF, EtOH, 4 h

2: 100 percent / 8 N Jones reagent / acetone / 2 h

3: 1.) t-BuLi, 2.) K₂CO₃ / 2.) acetone

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; dihydrogen peroxide; tert.-butyl lithium; potassium carbonate; In acetone;

DOI:10.1021/jo00228a028

upstream raw materials:

diazomethane

Methyl formate

methyl (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate

(E)-(3R,4S)-4-Methoxy-3-methyl-6-phenyl-hex-5-enoic acid

Refernces

Total synthesis of (±)-oudemansin

10.1016/S0040-4039(00)87009-4

The research focuses on the total synthesis of (+)-oudemansin, an antibiotic with potent antifungal properties, originally isolated from Oudemansiella mucida. The purpose of the study was to develop a synthetic route to (+)-oudemansin starting from N-cinnamaldehyde, utilizing a stereoselective Zn(BH4)2 reduction of β-keto ester as a key step. The synthesis involved a series of chemical reactions, including the Reformatsky reaction, oxidation with PDC, Zn(BH4)2 reduction, methylation using Me3Al and 1,8-bis(dimethylamino)naphthalene (Proton Sponge), hydrolysis with LiOH, and a Wolff rearrangement with silver benzoate. The synthesized (+)-oudemansin was confirmed by comparing its spectral data (IR and NMR) with that of the natural oudemansin, showing identical results. The study concluded that the synthetic route was successful in producing (+)-oudemansin, with the major isomer's C12-H being cis-oriented to the carbonyl group, as indicated by NMR spectra.