ECO-FRIENDLY SOLID STATE PHOTODECARBONYLATION FOR THE SYNTHESIS OF BIOLOGICALLY ACTIVE NATURAL PRODUCTS (SU833911)
Description:
Through our partnership with Merck, we will explore ways to harvest the sun’s ultraviolet radiation to take this reaction from the academic laboratory to the industry where it will be used to make many valuable medicines available to people who need them. Additionally, we plan bringing the fundamental concepts of green chemistry as they apply to industry to our graduate school curriculum by inviting a speaker from Merck to interact with graduate students.
Purpose/Objective:
Complex natural products pose challenges to sustainability because complex molecules often require chemical auxillaries or vast quantities of solvents in their syntheses and purification before they can be used as medicines. The difficulty in the syntheses of such compounds and the waste associated with their synthesis is evident by the fact that in 2005, pharmaceuticals and medicines produced 500 million tons of toxic waste. A significant obstacle in the synthesis of many natural products is the formation of adjacent quaternary carbon centers, sterically hindered carbon atoms with four different substituents.
Record Details:
Record Type: PROJECT (ABSTRACT)
Start Date: 08/15/2008
Completion Date: 08/14/2009
Record Last Revised: 11/13/2008
Record Created: 11/13/2008
Record Released: 11/13/2008
Record ID:
200632
Keywords:
green chemistry, solid state, photodecarbonylation, adjacent quaternary centers, natural products, toxic use reduction, solvent-free,,
Related Organizations:
Role: OWNER
Organization Name: UNIVERSITY OF CALIFORNIA - LOS ANGELES
Mailing Address: 405 Hilgard Ave
Citation: Los Angeles
State: CA
Zip Code: 90024
Project Information:
Approach: Our project to the address this challenge is a green chemistry methodology for synthesizing the molecular skeleton containing the adjacent quaternary centers using sunlight. Our approach will be to synthesize a ketone with quaternary carbon centers at the two alpha positions and then photodecarbonylate in the solid state to remove the ketone and form the bond between the two adjacent quaternary centers. By taking advantage of the chemical information trapped in a crystal lattice, solid state photodecarbonylation does not require any chemical auxiliaries, protection/deprotection, or purification since only one product is formed, thereby eliminating the use of toxic solvents and creation of unused byproducts. Since ketones are generally photo-excited in the UV region of the spectrum, ambient sunlight is sufficient to excite the molecule and therefore photodecarbonylate. The product of the photodecarbonylation will be a molecule with the adjacent quaternary centers. A group of hexahydropyrroloindole alkaloids can be synthesized from this decarbonylated molecule in a few steps.
Cost: $10,000.00
Research Component: Pollution Prevention/Sustainable Development
Project IDs:
ID Code: SU833911
Project type: EPA Grant