Abstract
The region above and away from C7 in the orvinols is known to be of particular importance in determining the μ-opioid receptor profile of this important class of opioids. However it has been difficult to explore this site due to the relative inaccessibility of 7β-substituted compounds. Here we report that perchloric acid induced epimerisation of the 7α-ketones (dihydrothevinones) allows considerably improved access to a series of β-ketones (β-dihydrothevinones). The extent of epimerisation of the 7α-ketone is determined by the degree of steric bulk in both the 6,14-bridge and in the ketone side chain.
| Original language | English |
|---|---|
| Pages (from-to) | 7571-7576 |
| Number of pages | 6 |
| Journal | Tetrahedron Letters |
| Volume | 41 |
| Issue number | 39 |
| DOIs | |
| Publication status | Published - 23 Sept 2000 |
Funding
This work was supported by NIDA (OTDP Medications Development Division) Grant DA 07315.
Keywords
- 7β-dihydrothevinones
- Epimerisation
- Opioids
- Thevinones
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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