An organocatalytic route to the synthesis of lactone moiety of compactin and mevinolin
β Scribed by Pradeep Kumar; Menaka Pandey; Priti Gupta; Dilip D. Dhavale
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- French
- Weight
- 259 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
The stereoselective Michael addition of alcohols dihydro-2tj-pyran-2-one afforded high yields of a key chiral portion of compactin and mevinolin. to 6-tosyloxymethyl-5,6synthon for the lactone Compactin (1) mevinolin (2) and related compounds have been cholesterol levels in animal models and man and
## Abstract Starting from (__R__)β__O__βbenzylglycidol and a sulfurβstabilized allyl anion, a (3 + 3) synthesis of the Ξ±,Ξ²βunsaturated (6__S__)βΞ΄βlactone 7 is achieved. Subsequent diastereoselective addition of a phenyldimethylsilyl cuprate and unmasking of the latent hydroxy function provides the
A new synthesis of racemic $-hydroxy-&lactone 10 with requisite relative stereochemistry as in compactin (la) is described utilizing cis-cyclohexane-1,3,5-trio1 (2) as the starting material. Compactin' (la) and mevinolin\* -(lb) have attracted a great deal of interest from synthetic organic chemists