Tetrahedron letters

Absolute configuration of insect-produced epilachnene

…, AB Attygalle, SR Smedley, T Eisner, J Meinwald

Index: Farmer, Jay J.; Attygalle, Athula B.; Smedley, Scott R.; Eisner, Thomas; Meinwald, Jerrold Tetrahedron Letters, 1997 , vol. 38, # 16 p. 2787 - 2790

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Citation Number: 20

Abstract

Samples of (R) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en-14-olide] were synthesized from (R) and (S)-norvaline. The diastereomericα-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 ...