Chiral palladium complexes with monoterpenoids oximes

Oximes of cis-caran-4-one, 3α- and 3β-hydroxycaran-4-ones, cis-verbanone, menthone, and 2β-hydroxybornan-3-one have been synthesized. The obtained oximes react with lithium tetrachloropalladate to give new chiral palladium complexes containing mono-or bidentate oxime ligands.     

Reaction of tris-(3-methyl-4,6-heptadienyl)-aluminum with carbon dioxide

Conclusions The reaction of tris--methyl-4,6-heptadienyl)aluminum with carbon dioxide leads to the formation of 4-methyl-5,7-octadienecarboxylic acid and tris--methyl-4,6-heptadienyl)carbinol.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1667–1668, July, 1973.     

Oxidative Transformations of Polyprenols

Oxidative transformationsinvolving the hydroxylsand -methylsof polyprenolsisolated from birch greenery (7-9 isoprene units in the chain) were used to produce ,-diols, diesters, aldehydoalcohols, and hydroxyacids. The products are of interest as potential anti-inflammatory, antiulcer, hepatoprotective, and cardio-active preparations.     

Simple synthesis of a terpenophenol—chlorin conjugate with an amide bond

A terpenophenol with a butylaminomethyl group was synthesized and conjugated to a chlorin macrocycle through formation of an amide bond without using activating reagents. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 561–563, November–December, 2007.     

An effective synthesis method for secondary fluorinated alcohols via the reaction of esters of polyfluorinated acids with trialkylalanes

Unlike nonfluorinated analogs, complex esters of polyfluorinated acids in reactions with trialkylalanes produce only polyfluorinated secondary alcohols.Department of Fine Organic Synthesis, Institute of Organic Chemistry, Urals Branch, Russian Academy of Sciences, 450054 Ufa. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 10, pp. 2339–2341, October, 1992.     

Synthesis of the Rhodiola rosea glycoside rosavin

A synthetic scheme was proposed for the glycoside rosavin that includes a one-step glycosylation of cinnamyl alcohol with a disaccharide. The structure of the product was confirmed by PMR and ¹³C NMR spectroscopy. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 323–324, July–August, 2006.     

Insect pheromones and their analogs

A four-stage asymmetric synthesis of (+)-disparlure [(7R,8S)-(+)-cis-methyl-7,8-epoxyoctadecane (V)] has been effected from 8-methylnon-2Z-en-l-ol (I), obtained by the carboalumination of acetylene with tris(5-methylhexyl)aluminum using the Sharpless reaction. The asymmetric epoxidation of (I), (Ar, mol. sieve A, (+)-DET, (iOPr)₄Ti, t-BuOOH, ?15°C, 20 h; H₂O, 1 h, NaOH, ?7°C, 30 min) gave 8-methyl-2S,3R-epoxynonan-l-ol (II), which was oxidized (kieselguhr-CrO₃-Py, 0°C, 2 h; 25°C, 2 h) to 8-methyl-2S,3R-epoxynonan-l-al (III). The coupling of (III) with n-C₈H₁₇CH=PPh₃ (?78°C, 1 h; 25°C, 15 h) gave 2-methyl-7R,8S-epoxyoctadec-9Z-ene (IV), the hydrogenation (H₂/5% Pd-C, 25°C, 5 days) of which led to (V) in admixture with an isomerization product. Compound (V) was isolated by HPLC. Substance, yield, [α] _D ²⁵ : (II), 73, ?2.75°; (III), 80, [80.8°; (IV), 50, +37.25°; (V), 50, +0.8°. The IR and PMR spectra of (II–IV), the¹³C NMR spectra of (II) and (III), and the mass spectrum of (IV) are given.