a Veterinary Toxicology and Entomology Research Laboratory, Agricultural Research, Science and Education Administration, U.S. Department o f Agriculture, College Station, TX 77840, b Western Regional Research Laboratory, Agricultural Research, Science and Education Administration, U.S. Department o f Agriculture, Berkeley, CA 94710, and c Department o f Entomology, University o f California, Ri...

(3Z,6Z,9S,10R)-9,10-Epoxy-3,6-henicosadiene (1) and (3Z,6Z,9S,10R)-9,10-epoxy-1,3,6-henicosatriene (5), pheromone components of the female fall webworm moth (Hyphantria cunea Drury), were synthesized by starting from (2S,3R)-2,3-epoxy-4-t-butyldimethylsilyloxy-1-butanol (8). Epoxide 8 was prepared by employing lipase-catalyzed asymmetric acetylation of ( )-8 as the key optical resolution step.

The epoxidation of alkenes was carried out over a CuO/Al(2)O(3) catalyst using cumene as an oxygen carrier, through a one-pot reaction, giving high conversion and selectivity with different substrates. Trans-β-methylstyrene gave the corresponding epoxide in 95% yield after 3 h.

A stereoselective total synthesis of the natural antibiotic (-)-8-O-methyltetrangomycin 1 is reported. The essential steps for this convergent synthesis are the transformation of a geraniol epoxide into a chiral octadiyne derivative, which was converted into a triyne. The cobalt-mediated [2+2+2] cycloaddition of the triyne led to a benz[a]anthracene system, which was oxidized with Ag(Py)(2)MnO(...

Ringing the changes: The total synthesis of the title compound centers around a novel strategy that employs a nickel(0)-phosphine complex and triethyl borane in an efficient closure of a 14-membered ring through C--C bond formation (see scheme; cod=cyclooctadiene). The synthesis was accomplished in 10 steps and in approximately 9 % overall yield.

On irradiation in the presence of Fe(CO)(5) under a CO atmosphere, the alkenyl cyclopropane 2 underwent smooth ring expansion to give the sesquiterpene (-)-delobabone 3. The alkenyl cyclopropane 2 was prepared from the enantiomerically enriched epoxide 1.

The reactivity of the C12-21 alkene of some erythromycin A derivatives was studied. This double bond was easily oxidized to the corresponding epoxide with excellent stereoselectivity. A single crystal X-ray structure showed that the epoxide moiety was on the same side as the acetonide. When an erythromycin derivative containing a C12-21 alkene was treated with diazomethane a [3+2] cycloaddition...

In the title ep-oxy monomer, C(24)H(22)O(5), the dihedral angle in the biphenyl residue is 3.34 (19)°, indicating a nearly coplanar conformation; this residue is not planar with the adjacent benzene ring [dihedral angle = 58.93 (14)°]. Each of the epoxide rings is disordered. Each epoxide ring was resolved over two alternative positions with site-occupancy ratios of 0.638 (10):0.362 (10) and 0....

The ring-opening of epoxides with potassium trifluoroborates proceeds smoothly in the presence of trifluoroacetic anhydride under metal-free conditions. The reactions are regioselective and afford a single diastereomer. Both electron-rich and electron-poor aryltrifluoroborates are tolerated.

A facile carbohydrate-based highly stereoselective synthetic route has been developed for the cytospolide P (1) from D-ribose for the first time. Key steps of the synthesis include Wittig homologation, regioselective epoxide ring opening, Sharpless asymmetric epoxidation, Evans aldol reaction, and Yamaguchi macrolactonization.