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
Synthesis of the hexahydrobenzofuran subunit of the milbemycins and the avermectins
β Scribed by Michael T. Crimmins; John G. Lever
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 228 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
π SIMILAR VOLUMES
Construction of the trisubstituted double bond of the Cl l-C28 subunit of avermectin Ala and Bla has been achieved in a five-step sequence.
A highly stereocontrolled route to the hexahydrobenzofuran subunit of the averzectins and the l ilbeuycins via an asymetric Dielsdlder reaction is described. The averuectins and the milbemycins are a fauily of uacrolide natural products, isolated from the broths of Streptomyces avermitilis
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