Vittatalactone, a β-Lactone from the Striped Cucumber Beetle, Acalymma vittatum

Abstract

A novel beta-lactone, vittatalactone (1), was isolated from collections of airborne volatile compounds from feeding male striped cucumber beetles, Acalymma vittatum. The structure of 1 was determined to be (3R,4R)-3-methyl-4-(1,3,5,7-tetramethyloctyl)oxetan-2-one by microderivatization, GC-MS, and NMR studies. The absolute configurations at C-2 and C-3 on the beta-lactone ring were assigned by use of the modified Mosher method, applied to the beta-hydroxy acid methyl ester resulting from methanolysis of 1. Biological activity of 1, possibly as an aggregation pheromone for A. vittatum, was indicated by electrophysiological studies using beetle antennae and by the production of 1 by feeding male, and not female, beetles.

Structure elucidation of female-specific volatiles released by the parasitoid wasp Trichogramma turkestanica (Hymenoptera: Trichogrammatidae)

“…Actually, we had to decide between 4 structures: syn , syn -, syn , anti -, anti , syn -, and anti , anti -configuration of the methyl groups at carbons 6, 8, and 10. Since semiochemicals representing saturated polydeoxypropionates typically show syn -configuration, suggesting general principles in enzymatic chain elongation [16,18], we hypothesized (2 E ,4 E ,6 S ,8 S ,10 S )-tetramethyltrideca-2,4-diene or its enantiomer to be the natural product.…”

The use of the lactone motif in chemical communication

“…Vittatalactone (9) and its minor nor-derivative 16 have been isolated from the striped cucumber beetle, Acalymma vittatum (Coleoptera: Chrysomelidae). 7 These male specic compounds show electrophysiological activity in antennae of both sexes, and were suggested to act as an aggregation pheromone, 7,8 but no behavioural studies have been reported. The absolute conguration shown has been deduced by total synthesis of the enantiomers.…”

Stereoselective Hydrogenation ofCCBonds: Application to Drug and Natural Product Synthesis

“…353 Acalymma vittatum can be synthesized in a short sequence employing two Ircatalyzed diastereoselective hydrogenations. 354 The latter was converted into corresponding hydroxy ester through transesterification with NaOMe and further converted into iodide 253 (Scheme 29.32).…”