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A series of (2-pyridyl)indoles was synthesized from the palladium(0)-mediated reaction of (1-(tert-nutyldimethylsilyl)-3- indolyl)zinc chloride and (1-(benzenesulfonyl)-2-indolyl)zinc chloride. The resulting products were utilized for the synthesis of the indolo[2,3-alpha]quinolizidine system via the stereoselective hydrogenation of thge pyridine ring followed by electrophilic cyclization in the indole 3-position.

The cyclization of pure all-cis 3-(2-piperidyl)indole was carried out to examine epimerization reactions at the C-2 and C-4 positions of the piperidine ring. Specifically, the piperidine-4-carboxylic acids obtained from the saponification of the 3-(2-piperidyl)indoles were reesterified with excess diazomethane. The results revealed that epimerization occurs at the C-2 position of the piperidine during alkaline hydrolysis of the ester.

Halogen-metal exchange from the corresponding 3-bromoderivative yields 1-(tert-butyldimethylsilyl)-3-lithioindole which reacts with electrophiles to form 3-substituted indoles. The N-silyl-3-lithioindole is of value in the synthesis of 3-substituted indoles due to the absence of ring fragmentation and rearrangement and the easy elimination of the protecting group.

Describes the palladium-catalyzed heteroarylation of 2- and 3-indolyzinc derivatives. Method for the preparation of (2-pyrisdyl)indoles; Demonstration of the potential of (2-pyridyl)indoles in the alkaloid synthesis; Study of the Pummerer cyclizations.

Describes the synthesis of a new fluorous allylstannane, (C6F13CH2CH2)3SnCH2-CH=CH2. Demonstration that the fluorous allylstannane's thermal reactions with aldehydes are roughly comparable to the reactions with the standard reagent Bu3SnCh2CH=CH2; Methodology used in study; Study's findings on fluorous allylstannane.