A hexahydrobenzoIABlfuran characteristic of the avermectins and certain milbemycins was synthesized via acid-catalyzed intramolecular addition of a diazoketone to a r-lactone; subsequent transformations led to structures containing much of the functionality and stereochemistry present in the corresp
Synthesis of the optically active hexahydrobenzofuran nucleus of the avermectins
✍ Scribed by D.R. Williams; F.D. Klingler; V. Dabral
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 320 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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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
## Abstract Optically active 1‐alkoxy‐ and 1‐amino‐3‐phospholene oxides were synthesized by the reaction of the corresponding 1‐chloro‐3‐phospholene oxides with (1__R__,2__S__,5__R__)‐(–)menthol and (__S__)‐(–)‐α‐phenylethylamine. The 3‐methyl‐3‐phospholene oxides were subjected to dichlorocyclopro