Several commercial Lewis acids, including those of the Bronsted type, specifically HBF(4).OEt(2), are able to catalyze the reaction between aromatic aldehydes and ethyl diazoacetate to produce 3-hydroxy-2-arylacrylic acid ethyl esters and 3-oxo-3-arylpropanoic acid ethyl esters. Reactions catalyzed by the iron Lewis acid [(eta(5)-C(5)H(5))Fe(+)(CO)(2)(THF)]BF(4)(-) (i.e., 1) have the best yields and greatest ratio of 3-hydroxy-2-arylacrylic acid ethyl ester. The product distribution of 1 is not affected in the presence of Proton Sponge, but is dependent on temperature and the nature of the substrate aldehyde, whereas the activity of HBF(4).OEt(2) is affected by the presence of Proton Sponge and is reactive at temperatures as low as -78 degrees C. Consequently, both 1 and HBF(4).OEt(2) are valuable catalysts in producing important 3-hydroxy-2-arylacrylic acid ethyl esters as precursors to biologically active compounds.

We have developed a convenient two-step procedure for the synthesis of 3-ethoxycarbonyl indoles from commercially available materials. The two-step procedure involves the synthesis of 2-aryl-3-hydroxypropenoic acid ester, followed by a catalytic reduction. This method is efficient, simple, and selective.

The documentation of hybrids between distantly related taxa can illustrate an initial step to explain how genes might move between species that do not exhibit complete reproductive isolation. In birds, some of the most phylogenetically distant hybrid combinations occur between genera. Traditionally, morphological and plumage characters have been used to assign the identity of the parental species of a putative hybrid, although recently, nuclear introns also have been used. Here, we demonstrate how high-throughput short-read DNA sequence data can be used to identify the parentage of a putative intergeneric hybrid, in this case between a blue-winged warbler (Vermivora cyanoptera) and a cerulean warbler (Setophaga cerulea). This hybrid had mitochondrial DNA of a cerulean warbler, indicating the maternal parent. For hundreds of single nucleotide polymorphisms within six regions of the nuclear genome that differentiate blue-winged warblers and golden-winged warblers (Vermivora chrysoptera), the hybrid had roughly equal ancestry assignment to blue-winged and cerulean warblers, suggesting a blue-winged warbler as the paternal parent species and demonstrating that this was a first generation (F1) hybrid between these species. Unlike other recently characterized intergeneric warbler hybrids, this individual hybrid learned to song match its maternal parent species, suggesting that it might have been the result of an extra-pair mating and raised in a cerulean warbler nest.

No abstract

Pleistocene climate cycles are well documented to have shaped contemporary species distributions and genetic diversity. Northward range expansions in response to deglaciation following the Last Glacial Maximum (LGM; approximately 21 000 years ago) are surmised to have led to population size expansions in terrestrial taxa and changes in seasonal migratory behaviour. Recent findings, however, suggest that some northern temperate populations may have been more stable than expected through the LGM. We modelled the demographic history of 19 co-distributed boreal-breeding North American bird species from full mitochondrial gene sets and species-specific molecular rates. We used these demographic reconstructions to test how species with different migratory strategies were affected by glacial cycles. Our results suggest that effective population sizes increased in response to Pleistocene deglaciation earlier than the LGM, whereas genetic diversity was maintained throughout the LGM despite shifts in geographical range. We conclude that glacial cycles prior to the LGM have most strongly shaped contemporary genetic diversity in these species. We did not find a relationship between historic population dynamics and migratory strategy, contributing to growing evidence that major switches in migratory strategy during the LGM are unnecessary to explain contemporary migratory patterns.