A MlchaeCAldol sequence of an enoate-ketone triggered by the action of an aluminum thiophenoxy "ate" complex leads to the oxahydrindene subunit of the avermectins.
Model studies directed toward the avermectins: A route to the spiroketal subunit
✍ Scribed by Francine E. Wincott; Samuel J. Danishefsky; Gayle Schulte
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 212 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Oxidative cyclization of a dihydropyran bearing a pendant alcohol is used to synthesize a spiroketal system of the type found in the avermectins.
📜 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 model spiroketal subunit 19, featuring the eastern fragment of okadaic acid has been assembled in three steps with full regio-and stereo-control.