Synthesis of Quinine Derived products

Quinine ( 1) and other related alkaloids are naturally occurring and are generally obtained by direct isolation from plants – especially the cinchona plants of South America.   Quinine has been used for treatment of malaria and is still a drug of last resort for management of the disease. Quinine has been widely used in many stereospecific/stereoselective organic transformations due to the presence of several chiral centers.   Dr. Sabila’s laboratory at Gallaudet is working on using quinine as a template for accessing new types of natural product-like libraries.   The various functional groups in quinine; alkene, alcohol, amine, aromatic positions, etc. will be exploited for traditional organic reactions like Ring-Closing and Cross-Metathesis, epoxidation, dimerization and various coupling reactions.   These protocols will enable new fairly complex molecules to be accessed in relatively few steps from quinine and related natural products.   The synthesized products will then be tested for a variety of biological activities including antimalarial, antiviral, anticancer and antibacterial activities in the hope of developing new classes of medicinal drugs.

1.   H3CO - N - HO- N Structure


Small molecule synthesis and Methodology

Dr. Sabila’s Undergraduate Research Laboratory at Gallaudet was designed with the aim of training students on basic organic synthesis research and instrumentation techniques.  This provides students with opportunities for on campus internship and acquisition of critical skills in preparation for off-campus internships or careers.  The projects are aimed at both the development of new transformations/methodologies and their application in preparing known or new types of small molecules and natural products that are usually challenging to access. Examples of these projects include ring expansions/ring contractions, silyl and other group migrations and coupling reactions.  So far, we have focused on the application of a new silyl-group ring-expansion protocol discovered during Dr. Sabila’s graduate school research.  We are also working on developing new transformation using imine intermediates. 

Image:  Fang Yang (Chemistry major), Dr. Paul Sabila, John Van Wey (Chemistry major), and Gaber Rupnik (Chemistry major) during a summer internship at Howard University.

Image:  Fang Yang (Chemistry major), Dr. Paul Sabila, John Van Wey (Chemistry major), and Gaber Rupnik (Chemistry major) during a summer internship at Howard University.