Publication

Synthetic Study towards Strictamine: The Oxidative Coupling Approach

2013
Journal Articles

Abstract

A synthetic approach featuring a key intramolecular oxidative coupling of a dianion for the formation of the C7–C16 bond was exploited aiming at the synthesis of strictamine. Treatment of substituted tetrahydrocarboline with LHMDS at –78 °C followed by iodine at room temperature afforded a tetracyclic compound, a substructure of eburnane-type alkaloid, via the formation of the Na–C16 bond.

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2013
Journal Articles

Abstract

Official source

Related concepts (11)

Stille reaction

The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes). A variety of organic electrophiles provide the other coupling partner. The Stille reaction is one of many palladium-catalyzed coupling reactions. Allyl, alkenyl, aryl, benzyl,acyl halides (Cl, Br, I), pseudohalides (OTf, OPO(OR)2), OAc The R1 group attached to the trialkyltin is normally sp2-hybridized, including vinyl, and aryl groups.

Kumada coupling

In organic chemistry, the Kumada coupling is a type of cross coupling reaction, useful for generating carbon–carbon bonds by the reaction of a Grignard reagent and an organic halide. The procedure uses transition metal catalysts, typically nickel or palladium, to couple a combination of two alkyl, aryl or vinyl groups. The groups of Robert Corriu and Makoto Kumada reported the reaction independently in 1972. The reaction is notable for being among the first reported catalytic cross-coupling methods.

Cyclic compound

A cyclic compound (or ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon (i.e., are carbocycles), none of the atoms are carbon (inorganic cyclic compounds), or where both carbon and non-carbon atoms are present (heterocyclic compounds with rings containing both carbon and non-carbon).

Related publications (1)

Synthetic Study towards Strictamine: The Oxidative Coupling Approach

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