Iodine-promoted ribosylation leads to a facile acetonide-forming reaction.

Iodine not only promotes smooth beta-selective glycosylation of ribose tetra-acetate under exceptionally mild conditions, it also catalyzes an expedient acetonide-forming reaction in this system when dry acetone is used as a solvent.

Kappa-opioid receptor-mediated effects of the plant-derived hallucinogen, salvinorin A, on inverted screen performance in the mouse.

Salvinorin A is a pharmacologically active diterpene that occurs naturally in the Mexican mint Ska Maria Pastora (Salvia divinorum) and represents the first naturally occurring kappa-opioid receptor agonist. The chemical structure of salvinorin A is novel among the opioids, and thus defines a new structural class of kappa-opioid-receptor selective drugs. Few studies have examined the effects of salvinorin A in vivo, and fewer still have attempted to assess the agonist actions of this compound at mu-opioid, delta-opioid, and kappa-opioid receptors using selective antagonists.

Radical deoxygenation of hydroxyl groups via phosphites.

A highly efficient, two-step sequence method for the deoxygenation of hydroxyl groups has been developed. The method involves the preparation of the 2-(2-iodophenyl)ethyl methyl phosphite derivative of an alcohol using methyl dichlorophosphite and 2-(2-iodophenyl)ethanol. Treatment of the phosphite intermediate with (n-Bu)3SnH/AIBN in refluxing benzene cleanly produces the deoxygenation product of the original alcohol.

A ring-rearrangement metathesis approach toward the synthesis of cyclopenta- and cyclohexa[c]indene systems.

[reaction: see text] A highly efficient synthesis of angularly fused tricyclic enones, cyclopenta- and cyclohexa[c]indene skeletons, has been achieved by the tether-directed ring-rearrangement metathesis sequence starting with readily accessible norbornene derivatives bearing allyl and homoallyl groups at the bridging carbon.

Total synthesis of (+)-acanthodoral by the use of a Pd-catalyzed metal-ene reaction and a nonreductive 5-exo-acyl radical cyclization.

[reaction: see text] The first total synthesis of the antibiotic acanthodoral (1) has been achieved from 3-methyl-2-cyclohexen-1-one in 19 steps in 2.1% overall yield. The synthesis features the use of a Pd-ene reaction in the presence of CO to form the endocyclic alkene 8, a nonreductive acyl radical cyclization reaction, and a ring contraction reaction by the Wolff rearrangement.