Abstract
Samples of (X) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en olide] were synthesized from (R) and (S)-norvaline. The diastereomeric α-methoxy-α-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) α-methoxy-α-trifluoromethylphenylacetyl chloride, were well resolved by gas chromatography. Analogous derivatization and gas chromatographic analysis of a sample of epilachnene from the pupal secretion of the coccinellid beetle, Epilachna varivestis, established that the natural product is (S)-epilachnene.
| Original language | English |
|---|---|
| Pages (from-to) | 2787-2790 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 38 |
| Issue number | 16 |
| DOIs | |
| State | Published - 21 Apr 1997 |