Abstract
The hydrophenanthrenone approach to the synthesis of morphinane alkaloids such as (-)-dihydrocodeinone (16) is described. Optical activity is achieved by chiral resolution of the hydrophenanthrenone derivative 6 on cellulose triacetate. Key steps of the thirteen-step synthesis are the conjugate addition of vinyl cuprate to 6, which generates the crucial benzylic quaternary center and the demethylative cycloetherification step that transforms bromoketone 8 into morphinane 9.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 475-482 |
| Number of pages | 8 |
| Journal | Chirality |
| Volume | 11 |
| Issue number | 5-6 |
| DOIs | |
| State | Published - 1999 |
Keywords
- Asymmetric synthesis of morphinane derivatives
- Chiral resolution by column chromatography
- Conjugate cuprate addition
ASJC Scopus subject areas
- Analytical Chemistry
- Catalysis
- Pharmacology
- Drug Discovery
- Spectroscopy
- Organic Chemistry