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Chemical Methods for the Synthesis of Complex Molecules

Award Number: R35GM161791
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)
PERIOD OF PERFORMANCE START DATE: 08/26/2026
PERIOD OF PERFORMANCE END DATE: 07/31/2031

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Chemical Methods for the Synthesis of Complex Molecules - SUMMARY Nitrogen-rich small molecules are essential components of modern medicines, and therefore critical to human health. As medical science has evolved, there has been a drive to develop more selective and potent pharmaceuticals that impart fewer side-effects while simultaneously tackling more complex diseases. At a molecular level, this has resulted in the need to rapidly access more structurally and topologically complex molecules that are able to differentiate between similar biological targets to effect the desired phycological response without unwanted side effects. These challenges continue to drive the need for more efficient synthetic methods to prepare complex nitrogen-containing small molecules. Historically, due to the high electronegativity of the nitrogen atom, small molecule nitrogen chemistry has largely focused on nucleophilic nitrogen centers. However, in recent years, there has been a growing realization that electrophilic nitrogen centers can be easily accessed, and that the reactivity of electrophilic nitrogen provides unique opportunities in the synthesis of complex nitrogen-containing molecules. Our group has contributed significantly to this shifting paradigm, particularly in the areas of aza-Heck cyclization to build complex, stereogenic nitrogen heterocycles and in developing chemistry to effect the C-alkylation of nitroalkanes to access complex nitroalkanes as advanced precursors to nitrogen-rich molecules. Manipulation of high-valent, electrophilic nitrogen centers is at the core of both of these research areas. In this program, we will continue to build on our significant track-record in electrophilic nitrogen chemistry to develop new methods to rapidly prepare complex organic molecules. Specifically, we will develop new Heck-like reactions of electrophilic nitrogen centers to access sterically congested, stereogenic nitrogen heterocycles, which are in high demand in modern medicinal chemistry but are challenging to prepare by other means. We will further investigate the mechanism of aza-Heck cyclization to discover how these reactions proceed, and use that understanding to further expand the synthetic horizons of this chemistry. Additionally, we will learn to control absolute stereochemistry in these cyclizations to selectively prepare single enantiomers of these complex molecules. To demonstrate the importance of aza-Heck cyclizations, we will also rapidly prepare several highly complex natural products with significant reported biological activity. Through collaboration, our synthetic efforts will enable biological follow-up studies to probe the modes of action of those compounds. Finally, using our recent discoveries in alkylation chemistry, we will pursue new synthetic methods to prepare and utilize complex nitroalkanes in the synthesis of medically relevant compounds. Overall, we expect that the development of this chemistry will positively impact human health by providing synthetic, medicinal, and process chemists valuable new tools for the construction of nitrogen-rich bioactive small molecules.


Issue Date FY	Funding FY	Legal Entity Name	Legal Entity Address	Legal Entity City	Legal Entity State	Legal Entity Zip Code	Legal Entity COUNTY	Legal Entity COUNTRY	Assistance Listing	Award Code	Budget Year	Action Date	Action Type	Action Amount

Issue Date FY: 2026 ( Subtotal = $479,532 )
2026	2026	UNIVERSITY OF DELAWARE	550 S COLLEGE AVE	NEWARK	DE	19713	NEW CASTLE	USA	Biomedical Research and Research Training	000	1	8/26/2026	NEW	$479,532
														Subtotal = $479,532

Grand Total All Awards = $479,532

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Chemical Methods for the Synthesis of Complex Molecules

Award Number: R35GM161791

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)

PERIOD OF PERFORMANCE START DATE: 08/26/2026

PERIOD OF PERFORMANCE END DATE: 07/31/2031

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