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Absolute configuration of the polyazamacrolides, macrocyclic polyamines produced by a ladybird beetle

✍ Scribed by Frank C. Schröder; Jay J. Farmer; Scott R. Smedley; Thomas Eisner; Jerrold Meinwald

Book ID: 104259780
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 211 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01404-x

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✦ Synopsis

The absolute configuration of the polyazamacrolides, oligomeric macrocycles from the pupal defensive secretion of Epilachna borealis, was determined by comparison of derivatives of the natural material with enantiomerically pure synthetic samples. Samples of a mixture of three ((9-1)-(2-hydroxyethylamino)alkanoic acids and of the corresponding aza-lactones were synthesized from (R)-alaninol. Gas chromatographic comparison of MTPA-amides of the synthetic aza-lactones with the MTPAamides of aza-lactones prepared from the natural material established that the polyazamacrolides have the (R)-configuration at all stereogenic centers.

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