Search

A new synthetic route to the indolo[2,3-a]quinolizidine system, involving the Pd(0)-catalyzed cross-coupling of a 2-indolylzinc derivative with a 2-halopyridine, stereoselective hydrogenation of the pyridine ring, and electrophilic cyclization upon the indole 3-position from the resulting 2-(2-piperidyl)indole, is reported.

Sulfides 2and 7are formed from sulfoxides 1and 4a, respectively, under Pummerer reaction conditions. The process involves the formation of a positively charged seven-membered ring intermediate by nucleophilic attack of the indole nucleus on the initially formed acyloxysulfonium salt.

Hydroxymethylation of organic halides 2using a catalytic amount of fluorous tin hydride 1, CO, and NaBH 3CN as a reducing agent, proceeded smoothly to give one-carbon homologated alcohols 5in good yields. Three phase workup (water-dichloromethane-perfluorohexane) was conveniently performed for the separation of 1and 5.

For Abstract see ChemInform Abstract in Full Text.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.