Merle A. Battiste

Carvone Oxide: An Example of Convergent Evolution in Euglossine Pollinated Plants

Trans-carvone oxide has been found in the floral fragrances of nine species of Ca- tasetum, one species each of Aspasia and Notylia (all three genera in Orchidaceae), and in one species of Dalechampia (Euphorbiaceae). Carvone oxide is a major fragrance component in 11 of the 12 species analyzed, and has been synthesized and used in field bioassays in Panama, where it attracts five species of Eulaema and three species of Euglossa. We predict it will be a major attractant of Eulaema species that previously have not been attracted to chemical baits. We suggest that synthesis and secretion of carvone oxide by several genera of Orchidaceae and one species of Euphorbiaceae are the result of evolutionary convergence in floral rewards.

Comparison of volatiles emitted by male caribbean and mexican fruit flies

Volatiles emitted byAnastrepha suspensa andAnastrepha ludens males were trapped and compared by GC-MS. Both species emitted previously reported nine-carbon alcohols, (Z)-3-nonenol and (Z,Z)-3,6-nonadienol, and epimeric lactones, anastrephin and epianastrephin. A third isomeric lactone, the macrolide suspensolide, which was previously known only fromA. suspensa is reported here for the first time in the volatiles ofA. ludens. We also report that both species released different proportions of the same three sesquiterpene hydrocarbons:α-farnesene,β-bisabolene, andα-trans-bergamotene. Theβ-bisabolene was isolated in sufficient quantity fromA. suspensa volatiles to establish its absolute configuration as the (R)-(+)-enantiomer. Some plausible biosynthetic relationships of farnesol to the isoprenoid lactones and sesquiterpenes identified in this study are discussed. Finally, we report thatA. suspensa produces the monoterpene (Z)-β-ocimene whileA. ludens volatiles contained limonene.

Anastrephin and epianastrephin, novel lactone components isolated from the sex pheromone blend of male caribbean and mexican fruit flies

Anastrephin and epianastrephin, novel lactone components isolated from the male produced pheromone of two Anastrepha fruit fly species (Caribbean and Mexican) are assigned the structure and relative stereochemistry 1 and 2, respectively, on the basis of spectroscopic and chemical evidence including synthesis.

Suspensolide, a new macrolide component of male caribbean fruit fly(anastrepha suspensa [loew]) volatiles

Abstract A novel macrolide was isolated from volatiles produced by male Caribbean fruit flies and identified as ( E , E )-4,8-dimethyl-3,8-decadien-10-olide, I, on the basis of spectroscopic and chemical evidence, including synthesis.

Stereoselective Peterson alkoxycarbonylmethylenation reaction of substituted cyclohexanones

In contrast to previous results the Peterson olefination reaction of substituted cyclohexanones with metallotrimethylsilylacetates (1) affords moderate to high stereoselectivity.

Total synthesis and structure proof of (3E,8E)-suspensolide

Abstract A new macrolide, E,E-suspensolide ( 1 ), was prepared in six steps from mesityl oxide. The stereochemistries of intermediate isomers were assigned principally from their 13 C NMR spectra. An isomeric macrolide, Z,E-suspensolide ( 2 ), was also prepared.

Trans-carvone oxide, a monoterpene epoxide from the fragrance of Catasetum

Abstract A new monoterpene epoxide trans -carvone oxide (1) has been isolated from the floral fragrance of Catasetum maculatum , characterized by spectral data and synthesized.

Pyrazole addition to Δ1-azirines. Structure of purported 2:1 adducts of Δ1-azirines with sym-tetrazines

The previously unestablished structure of purported 2:1 adducts isolated from the reaction of Δ1-azirines with s-tetrazines is now shown to be identical with the aziridine derivatives resulting from thermally promoted addition of pyrazoles to Δ1-azirines.

Reactivity and regiochemical behavior in the solvolysis reactions of (2,2-difluorocyclopropyl)methyl tosylates

The rate constants for acetolysis of (2,2-difluorocyclopropyl)methyl tosylate, and (2,2-difluoro-3-methylcyclopropyl)methyl tosylate at 92 °C and of 1-(2,2-difluorocyclopropyl)ethyl tosylate at 42 °C are reported and the reactivities and regiochemistries of ring opening of these systems are discussed and compared with expectations based on computational results. The results are discussed in terms of the use of (2,2-difluorocyclopropyl)methyl systems as mechanistic probes.

Synthesis of aminophenyl and methoxyphenyl perfluoroalkyl ketones

Abstract The title compounds are obtained by direct hydrolysis of the corresponding 2/4-perfluoroalkyl-substituted anilines and anisoles by the system AcOH/HBr/H 2 O/Al 2 O 3 . A two-step preparation of 2/4-perfluoroacylanilines involves the treatment of the 2/4-perfluoroalkylaniline with sodium ethoxide followed by hydrolysis of the resultant diethyl acetal with hydriodic acid.