The Synthetic Routes of (7a,17b)-7-(9-Bromononyl)estra-1,3,5(10)-triene-3,17-diol

The synthesis of complex organic molecules is a crucial aspect of the chemical industry.
One such molecule is (7a,17b)-7-(9-bromononyl)estra-1,3,5(10)-triene-3,17-diol, a naturally occurring compound with potential medicinal properties.
There are several synthetic routes for this molecule, each with its own advantages and disadvantages.

One of the most common methods for synthesizing this compound involves a sequence of reactions known as the Pictet-Spengler reaction, the Claisen condensation, and the Widder synthesis.
This route begins with the synthesis of the phenylprolinolic ester intermediate, which is then treated with potassium hydroxide to create the corresponding phenylprolinolic amide.
This intermediate is then subjected to a Pictet-Spengler reaction, which involves the use of a strong base such as sodium hydroxide to form a substituted phenylprolinolic amide.
This intermediate is then treated with an alcohol in the presence of a strong acid catalyst, such as hydrochloric acid, to form the final product.

Another synthetic route for (7a,17b)-7-(9-bromononyl)estra-1,3,5(10)-triene-3,17-diol involves the use of a Grignard reagent.
This method involves the treatment of a brominated derivative of the target molecule with magnesium metal to form a Grignard reagent.
This reagent is then treated with an alcohol in the presence of a strong acid catalyst, such as hydrochloric acid, to form the final product.

A third synthetic route for (7a,17b)-7-(9-bromononyl)estra-1,3,5(10)-triene-3,17-diol involves the use of a Suzuki-Miyaura reaction.
This method involves the use of a boronic acid derivative of the target molecule and a palladium catalyst to form a carbon-carbon bond.
This intermediate is then treated with an alcohol and a strong acid catalyst, such as hydrochloric acid, to form the final product.

Each of these synthetic routes has its own advantages and disadvantages.
The Pictet-Spengler reaction route is relatively simple and can be performed using readily available reagents.
However, it requires the use of strong bases and acids, which can be hazardous to handle.
The Grignard reagent route is more efficient and less hazardous than the Pictet-Spengler reaction route, but it requires the preparation of a Grignard reagent, which can be time-consuming and requires specialized equipment.
The Suzuki-Miyaura reaction route is the most efficient and least hazardous of these three methods, but it requires the use of a palladium catalyst, which can be expensive and difficult to handle.

Overall, the selection of a synthetic route for (7a,17b)-7-(9-bromononyl)estra-1,3,5(10)-triene-3,17-diol depends on several factors, including the availability of reagents, the scale of the synthesis, and the safety and efficiency of the method.
Each of these routes has its own merits and drawbacks, and the choice of the best route will depend on the specific needs of the synthesis.