Question

Brucine is a poisonous alkaloid obtained from Strychnosnux vomica, a tree that grows in India, Sri Lanka, and northern Australia. Write out a resolution scheme similar to the one given in Section 29.3A, which shows how a racemic mixture of phenylalanine can be resolved using brucine

Short answer

Answer

Step-by-step solution

Brucine

Brucine comes under the category of alkaloids and is connected to strychnine. It is employed for stereospecific chemical syntheses in synthetic chemistry.

Resolution of a mixture of phenylalanine using brucine

The free amino group of the amino acid phenylalanine forms an amide bond on reaction with acetic anhydride. The product formed from the reaction is N-acetyl amino acid:

The reaction of phenylalanine with acetic anhydride

The enantiomers of phenylalanine undergo proton transfer with brucine to form diastereomers as:

Diastereomers formed by proton transfer

The physical and chemical properties of diastereomers are different from each other. The hydrolysis of diastereomers produces enantiomers of phenylalanine.