Question

What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson’s disease? These steps are the key reactions in the first commercial asymmetric synthesis using a chiral transition metal catalyst. This process was developed at Monsanto in 1974.

Short answer

Answer

The steps needed to convert A to L-dopa is shown as:

Step-by-step solution

L-dopa

L-dopa is an organic compound containing amino groups and is used to treat the symptoms linked with Parkinson’s disease. It can be synthesized from L-Tyrosine, and dopamine is synthesized from L-dopa.

Steps needed to convert A to L-dopa

When A is treated with ${\mathrm{H}}_2$ in the presence of a chiral Rh catalyst, an alkene is reduced to alkane. On further treatment with a strong acid, the ${\mathrm{NHCOCH}}_3$(amide group) is converted to ${\mathrm{NH}}_2$ (amine group), the methoxy group to OH, and the $C{H}_{3}COO$group to OH.

This leads to the formation of L-dopa. The steps required to convert A to L-dopa is shown as:

synthesis of L-dopa