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Synthesis of Dihydrobenzofuran Natural Products that Modulate Immune Response

Award Number: R16GM158919
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: 08/10/2026
PERIOD OF PERFORMANCE END DATE: 03/31/2030

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Synthesis of Dihydrobenzofuran Natural Products that Modulate Immune Response - Project Summary Dihydrobenzofuran natural products, such as maceneolignan A, are small heterocyclic molecules that exhibit a variety of bioactive properties including anti-inflammatory, anticancer, antiviral, and antifungal activity. Maceneolignan A has demonstrated efficacy in inhibiting chemokine receptor signaling, which plays a role in diseases characterized by inflammatory response such as allergic reactions, asthma, arthritis, inflammatory bowel disease, multiple sclerosis, and Alzheimer’s disease. While some natural products can be easily isolated from natural sources, the ability to prepare the same molecules in the laboratory can allow for structural modifications to improve potency. The goal of this project is to develop and implement a new synthetic approach to prepare arylated bioactive dihydrobenzofurans that is amenable to late-stage diversification. Our strategy will rely on optimization of a key Ni-catalyzed cross-coupling reaction that appends the aromatic ring at the final step in the synthesis, ultimately providing a divergent approach that significantly reduces the number of steps required to prepare structural analogs. To address this objective, we will investigate the use of bench-stable N- hydroxyphthalimide (NHP) esters and aryl iodides as cross-coupling reagents. This type of cross-coupling reaction is quite robust but has not been demonstrated on dihydrobenzofurans. We will first optimize the required cross-coupling reaction using various strategies, and will then apply the optimal conditions to the synthesis of five natural products (maceneolignan A, maceneolignan B, licarin A, licarin B, and acuminatin) and synthetic analogs. Through collaboration with the Fraser lab at CSULB, synthesized dihydrobenzofuran compounds will be evaluated for their potential to modulate immune response in macrophage cell lines. It is expected that this study will provide new knowledge in the application of cross-coupling reactions towards the synthesis of bioactive dihydrobenzofurans and begin to answer questions about how dihydrobenzofuran natural product analogs influence immune response. This interdisciplinary project is expected to provide enhanced research opportunities for undergraduate students at CSULB.


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 = $146,819 )
2026	2026	CALIFORNIA STATE UNIVERSITY LONG BEACH RESEARCH FOUNDATION	6300 E STATE UNIVERSITY DR STE 332	LONG BEACH	CA	90815	LOS ANGELES	USA	Biomedical Research and Research Training	000	1	8/7/2026	NEW	$146,819
														Subtotal = $146,819

Grand Total All Awards = $146,819

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Synthesis of Dihydrobenzofuran Natural Products that Modulate Immune Response

Award Number: R16GM158919

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: 08/10/2026

PERIOD OF PERFORMANCE END DATE: 03/31/2030

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