Tetrahedron Letters p. 2787 - 2790 (1997)
Update date:2022-08-05
Topics:
Farmer, Jay J.
Attygalle, Athula B.
Smedley, Scott R.
Eisner, Thomas
Meinwald, Jerrold
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.
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(1997)
