A model study for the synthesis of the hexahydrobenzofuran fragment of the milbemycins and avermectins.
โ Scribed by Alan P. Kozikowski; Keith E. MaloneyHuss
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 230 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
Radical-induced intramolecular Michael cyclization of a bromovinyl-type appendage onto a functionalized cyclohexene carboxylic acid derivative produces the corresponding oxahydrindanes which can be transformed into oxahydrindenes (hexahydrobensofurans) related to the title compounds. (-)-Quinic acid
The efficient synthesis of C-l to C-10 monocyclic nonaromatic fragments of the milbemycins and avermectins has been achieved, in which the key step involved the stereoselective addition of 2-lithio-4-phenylthiobut-1-ene to a 3-hydroxycyclohexanone derivative.
A highly regio-and stereoselective Diels-Alder reaction between dienophiles of type I and dienes of type I1 (Scheme I ) gives rise to Diels-Alder adducts of type 111. Upon treatment with BF,. Et,O, these adducts are smoothly converted into the corresponding enones (Scheme 6). Under mild acidic condi
A highly stereocontrolled synthesis of the Cl 1 to C3 1 fragment of the potent antimicrobial agent milbemycin D has been completed. This approach utilizes a unique hydrolysis-cyclization to construct the spiroketal portion of the molecule. The milbemycins 2 and the avermectins3 are two structurall
Oxidation of the mixture of products obtained by treatment of (S)-2-methylbutanal 8 with the E-but-2-enyldi-isopinocampheylborane prepared from (+)-pinene gave a mixture of homoallylic alcohols from which the major isomer 9 was isolated by chromatography. Oxidation with vanadylacetoacetate and ten-b