A step in the formation of Batzelladine requires firebending, waterbending, and airbending. Master them all!
Click on any of the three links below to visit the fire nation, water tribe, or the air nomads to learn the specific mechinism involved in the alkene metathesis, hydrogenation, and deprotection,
Note: The first step of our reaction mechanism is alkene metathesis. In the second step, hydrogenation and deprotection occur concurrently, as H2 and Pd(OH2) is added to the reaction mixture. In this tutorial, the hydrogenation step and deprotection steps are treated as seperate steps in order to simplify the overall mechanism..
As a young undergraduate in North Carolina, John Montgomery began his journey to becoming the avatar by learning the process of alkene metathesis from the master of firebending, Professor Maurice Brookhart. In this step, the Grubbs Second Generation Catalyst is used to attach the TBDPS ether of hept-6-en-1-ol to the end of the carbon chain in the starting material; an ethene byproduct is generated as a result of this process.
The final element that Montgomery mastered was water when he moved to the seaside city of Irvine, California. Under Professor Larry E. Overman, Montgomery mastered the art of hydrogenation. In this step, Palladium on carbon is used to hydrogenate the product of the first step to transform the alkene to a single bond.
After mastering fire, Montgomery moved to Colorado and mastered the element of air in the state home to “fresh air and fond memories.” He learned how to remove protecting groups and allow reactions to proceed. In the final step of this reaction mechanism, the benzyl group and p-methoxybenzyl group are removed to allow further reaction steps to take place.