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(-) Lobeline: total synthesis and derivitization

Institution: California Institute of Technology
Investigator(s): Jeffrey Bagdanoff, B.S.
Award Cycle: 2002 (Cycle 11) Grant #: 11DT-0193 Award: $60,000
Subject Area: General Biomedical Science
Award Type: Dissertation Awards

Initial Award Abstract
It is widely understood that quitting smoking is a very difficult and often unsuccessful endeavor for millions of Americans. While the psychological aspects of altering ones lifestyle pose significant barriers to “kicking the habit’, the intense physiological dependence of nicotine is also directly responsible for relapse. Lobeline is a natural product known to mimic the effect of nicotine by interacting directly with nicotine receptors.

Extracts of lobeline have been formulated and widely used to treat nicotine withdrawal. Furthermore, the natural product is an effective treatment for respiratory ailments such as asthma, bronchitis, pneumonia, and whooping cough. In this proposal, a new synthetic method will be applied to the concise synthesis of lobeline. While there is an easily accessible natural abundance of lobeline (derived from lobelia inflata, commonly known as “indian tobacco”) the lack of an efficient synthetic route restricts potential for biological analysis baised on chemical modification.

The proposed synthesis will provide a basis for accessing multiple drug-like compounds related to the parent natural product. Biological evaluation of the thousands of potential analogues may ultimately provide a drug with medicinal properties superior to the natural parent compound, resulting in improved respiratory and nicotine withdrawal therapies.

Palladium-catalyzed oxidative kinetic resolution with ambient air as the stoichlometric oxidation gas.
Periodical: Angewandte Chemie (International Ed. in English) Index Medicus:
Authors: Bagdanoff JT, Stoltz BM ART
Yr: 2004 Vol: 43 Nbr: 3 Abs: Pg: 353

Palladium-catalyzed enantioselective oxidation of alcohols: a dramatic rate acceleration by Cs2CO3/t-BuOH.
Periodical: Org. Lett Index Medicus:
Authors: Bagdanoff JT, Ferreira EM, Stoltz BM ART
Yr: 2003 Vol: 5 Nbr: 6 Abs: Pg: 835