Analysis by gas chromatography/mass spectrometry (GC/MS) of volatiles from virgin female emerald ash borer, Agrilus planipennis Fairmaire confirmed the emission of (3Z)-lactone [(3Z)-dodecen-12-olide] but not its geometric isomer, (3E)-lactone [(3E)-dodecen-12-olide]. Gas chromatographic/electroantennographic (GC/EAD) analysis of synthetic (3Z)-lactone, which contained 10% (3E)-lactone, showed a strong response of male and female antennae to both isomers. EAG analysis with 0.01- to 100-μg dosages showed a positive dose response, with females giving significantly higher responses than males. In field experiments with sticky purple prism traps, neither lactone isomer affected catches when combined with ash foliar or cortical volatiles (green leaf volatiles or Phoebe oil, respectively). However, on green prism traps, the (3Z)-lactone significantly increased capture of male A. planipennis when traps were deployed in the canopy. Captures of males on traps with both (3E)-lactone and (3Z)-hexenol or with (3Z)-lactone and (3Z)-hexenol were increased by 45-100%, respectively, compared with traps baited with just (3Z)-hexenol. In olfactometer bioassays, males were significantly attracted to (3E)-lactone, but not the (3Z)-lactone or a 60:40 (3E):(3Z) blend. The combination of either (3E)- or (3Z)-lactone with Phoebe oil was not significantly attractive to males. Males were highly attracted to (3Z)-hexenol and the (3Z)-lactone + (3Z)-hexenol combination, providing support for the field trapping results. These data are the first to demonstrate increased attraction with a combination of a pheromone and a green leaf volatile in a Buprestid species.

Current approaches to the treatment of cognitive and behavioral symptoms of Alzheimer disease emphasize the use of cholinesterase inhibitors. The kinetic effects of the cholinesterase inhibitors donepezil, galantamine, metrifonate, physostigmine, rivastigmine, and tetrahydroaminoacridine were examined with respect to their action on the esterase and aryl acylamidase activities of human acetylcholinesterase (AChE) and human butyrylcholinesterase (BuChE). Each of these drugs inhibited both AChE and BuChE, but to different degrees. Inhibition of BuChE by these compounds was approximately the same, or better, when acetylthiocholine, the analog of the neurotransmitter acetylcholine, was used as the substrate, instead of butyrylthiocholine. In addition, for these drugs, the inhibition of aryl acylamidase activity paralleled that observed for inhibition of esterase activity of AChE and BuChE. Given that drugs that are currently in use for the treatment of Alzheimer disease inhibit both AChE and BuChE, the development of drugs targeted toward the exclusive inhibition of one or the other cholinesterase may be important for understanding the relative importance of inhibition of BuChE and AChE in the treatment of this disease.

The male-produced aggregation pheromones of Tetropium fuscum (F.) and T. cinnamopterum Kirby were identified as (2S,5E)-6,10-dimethyl-5,9-undecadienol by chemical analysis, synthesis, electronantennography, and field trapping; the compound is here renamed "fuscumol". The effect of fuscumol chirality, alone or with host volatiles, and fuscumol release rate on Tetropium spp. was tested in field-trapping experiments in Nova Scotia and Poland. Both (S)-fuscumol and racemic fuscumol synergized trap catches of male and female T. fuscum, T. cinnamopterum, and T. castaneum (L.) when combined with a blend of host monoterpenes and ethanol. Without added host volatiles, fuscumol was either unattractive (in Nova Scotia) or only slightly so (in Poland). (R)-Fuscumol, alone or in combination with host volatiles, did not elicit increases in trap capture of any Tetropium species, relative to the controls. Fuscumol synergized attraction of both sexes to host volatiles, thus indicating it acts as an aggregation pheromone. Sex ratio was often female-biased in traps baited with fuscumol plus host volatiles, and was either unbiased or male-biased in traps with host volatiles alone. In traps with host volatiles and racemic fuscumol, mean catches of Tetropium species were unaffected by fuscumol release rates ranging from 1 to 32 mg/d. The attraction of three different Tetropium species to the combination of (S)-fuscumol and host volatiles suggests that cross-attraction may occur where these species are sympatric, and that reproductive isolation possibly occurs via differences in close-range cues. These results have practical applications for survey and monitoring of T. fuscum, a European species established in Nova Scotia since at least 1980, and for early detection of T. castaneum, a European species not presently established in North America.

Male Tetropium fuscum (F.) and T. cinnamopterum Kirby mated with live and dead (freeze-killed) conspecific females upon antennal contact, but did not respond to dead females after cuticular waxes were removed by hexane rinsing. Significantly fewer males of each species attempted to copulate with live or dead heterospecific females than with conspecifics, indicating that mate recognition was mediated by species-specific contact sex pheromones in the female's cuticular hydrocarbons. GC/MS analysis of T. fuscum elytra identified n-alkanes and mono-methyl branched alkanes of which 11-methylheptacosane and 3- and 5-methyltricosanes were dominant in females. Full male responses, including copulatory behavior, were restored with application of enantiomerically pure synthetic (S)-11-methyl-heptacosane at 40 μg/female (one female equivalent) but not with racemic or (R)-11-methyl-heptacosane. The cuticular hydrocarbons on T. cinnamopterum elytra included 11-methyl-heptacosane as well as n-alkanes, methyl-branched alkanes, mono-alkenes, and (Z, Z)-6, 9-alkadienes. (Z)-9-pentacosene, (Z)-9-heptacosene, and 11-methyl-heptacosane were female dominant, but only (Z)-9-pentacosene elicited precopulatory behaviors in conspecific males at levels similar to those behaviors elicited by unrinsed females, but elicited copulation in fewer than half of males. At female equivalent dosages (10 μg), neither (Z)-9-heptacosene nor (S)-11-methyl- heptacosane elicited responses in males that were significantly different from those responses to a rinsed female but when applied together, the proportion of males responding was significantly increased. 11-methyl-heptacosene is thus a contact pheromone component common to both species, which may explain the heterospecific mating attempts by some males.

A total synthesis of the marine alkaloid manzamine C has been accomplished. A Ramberg-Bäcklund reaction was used as a key step to construct the required azacycloundecene ring.Key words: alkaloid, macrocycle, Ramberg–Bäcklund, manzamine C.

A convenient one-step method for the preparation of alkynyl phenyl sulfides using diphenyl disulfide has been developed. The oxidation of the corresponding sulfides to the sulfoxides, and not sulfones, was achieved by using trans-(phenylsulfonyl)-3-phenyloxaziridine. A variety of other oxidizing reagents was also investigated.

Diastereoselective trapping of chiral enantiopure oxyallyl cations by common dienes is reported. Excellent diastereoselectivities were obtained and depending on which auxiliary was used cycloadditions proceeded through a chelated or non‐chelated pathway. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

The brown spruce longhorn beetle, Tetropium fuscum (F.), is an invasive wood-boring species in eastern Canada. Gas chromatographic/electroantennographic (GC/EAD) analyses of Norway and red spruce volatiles detected a number of consistent EAD-active responses to compounds that are known to be stress-induced in spruce. The effects of these EAD-active compounds on various aspects of adult behavior were tested. In two-choice olfactometer assays, a monoterpene spruce blend, (R)-(-)-linalool, (3Z,6E)-α-farnesene, (E)-β-farnesene and spruce essential oil were attractive to both sexes. However, when they were combined with the male-produced pheromone (fuscumol), they elicited a sex-specific response: females were significantly attracted to combinations of fuscumol plus either (3Z,6E)-α-farnesene, (E)-β-farnesene and spruce essential oil but males were not. Fuscumol alone was unattractive to either sex in the olfactometer. Males exposed to fuscumol, (3Z,6E)-α-farnesene, or a combination of both, but not (E)-β-farnesene, were more likely to engage in the pheromone calling posture relative to controls. Both the monoterpene spruce blend and spruce essential oil elicited significantly greater trap capture of both sexes of T. fuscum in the presence of fuscumol and ethanol than (3Z,6E)-α-farnesene or (R)-(-)-linalool, which did not elicit trap capture alone or in combination with fuscumol. The data support the hypothesis that stress-induced sesquiterpene components, such as (3Z,6E)-α-farnesene, are important for mediating close-range attraction and behavior in T. fuscum while the monoterpene components are important for long-range processes (trap capture).