![Obolactone Structure](https://www.chemicalbook.com/CAS/20150408/GIF/712272-88-3.gif)
Obolactone
- Product NameObolactone
- CAS712272-88-3
- CBNumberCB92725441
- MFC19H18O4
- MW310.34
- MDL NumberMFCD32644959
- MOL File712272-88-3.mol
Chemical Properties
Melting point | 116-118℃ |
Boiling point | 522.2±49.0 °C(Predicted) |
Density | 1.270±0.06 g/cm3(Predicted) |
Obolactone Price
Product number | Packaging | Price | Product description | Buy |
---|---|---|---|---|
Crysdot CD32000554 | 5mg | $922 | Obolactone 95+% |
Buy |
Obolactone Chemical Properties,Usage,Production
Definition
ChEBI: Obolactone is a pyranone isolated from the trunk barks of Cryptocarya obovata and has been shown to exhibit cytotoxicity against the KB cell line. It has a role as an antineoplastic agent and a plant metabolite. It is a member of 2-pyranones and a member of 4-pyranones.Synthesis
The synthesis of (+)-obolactone (14, Scheme 3) by Brückner and Walleser employed the same conditions from the synthesis of 17-deoxyroflamycoin to transform bis-epoxide R,R-4 to bis-homoallylic diol S,S-8. Diol 8 was then protected using 2,2-dimethoxypropane under acidic conditions to provide acetonide 12 in 95% yield. One of the alkene functional groups of the C2- symmetric acetal underwent a subsequent symmetry-breaking Wacker oxidation. Treatment of acetonide 12 with catalytic PdCl2 under an atmosphere of oxygen using CuCl as the stoichiometric oxidant afforded a 64% yield of methyl ketone 13, with over-oxidation to the diketone also observed (18% yield). The methyl ketone functionality of 13 was critical for the installation of the dihydro-g-pyranone moiety in the natural product, while the syn-orientation of the C–O bonds was achieved through Mitsunobu inversion of the lactone stereocenter. Brückner and Walleser specifically mention that while Krische and co-workers have reported on an impressive single-step procedure for the catalytic enantioselective synthesis of bishomoallylic diol (S,S-4) from 1,3-propanediol, and have used this method extensively in the synthesis of polyketide natural products, 21,22 the high cost of catalyst and ligand precluded their use on scale in this case.![(+)-obolactone synthesis (+)-obolactone synthesis](/NewsImg/2024-06-03/6385300714937200915870807.png)
Preparation Products And Raw materials
Obolactone Suppliers
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