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New methods to prepare 1,4-oxazin-2-ones and applications in the construction of polysubstituted pyridines

Award Number: R15GM107702
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: 09/01/2014
PERIOD OF PERFORMANCE END DATE: 08/31/2026

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New methods to prepare 1,4-oxazin-2-ones and applications in the construction of polysubstituted pyridines - Project Summary This proposal describes the development of new methods for the preparation of 1,4-oxazinone precursors and seeks to apply these intermediates to the construction of highly substituted pyridine products through a merged cycloaddition/cycloreversion process. Oxazinones are computationally and experimentally the most reactive precursor in cycloaddition/cycloreversion sequences leading to pyridines, yet remain understudied and underutilized. The new synthesis methods proposed for construction of oxazinones are direct, employ common starting materials, and are supported by preliminary data. The planned applications of oxazinones for the construction of polysubstituted pyridines will increase our understanding of the fundamental reactivity of this heterocyclic ring system and seek to reveal some of the potential of oxazinones relative to other [4+2]/retro[4+2] heterocycles used in pyridine synthesis. Pyridines are one of the most prevalent structures imbedded within biologically active molecules. Thus, new methods for the construction of pyridine motifs (especially those not easily accessed through other methods) is merited and is acutely significant to the biomedical sciences. In addition to foundational research, applications directed toward the synthesis of potentially biologically relevant structures are included in the proposal. These include (1) a unified synthesis strategy toward xylanigripone A and B, unique members of the ergot alkaloid family that display pyridine and piperidine structures and (2) studies directed to the conversion of the b-amino alcohol function in peptides bearing N-terminal serine and threonine residues into reactive oxazinone intermediates. Computational efforts are proposed to compare peptide- derived oxazinones prepared in this manner to other Diels-Alder reactive substrates, a prelude to possible downstream bioconjugation applications. William & Mary does not offer a doctoral degree in chemistry (BS/MS only); accordingly, my research group is composed of undergraduate researchers (and one MS candidate). My current research program creates a rigorous environment for learning and enforces teaching and training in the one-on-one research experience. The proposed research would continue within this climate and is designed at an appropriate level for students to make progress. Support from the NIH would enable the research of 3-4 undergraduates and one Master's candidate for each year of the award.


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: 2024 ( Subtotal = $0 )
2024	2023	COLLEGE OF WILLIAM AND MARY	1314 S MOUNT VERNON AVE	WILLIAMSBURG	VA	23185	JAMES CITY	USA	Biomedical Research and Research Training	001	3	2/21/2024	COMPETING CONTINUATION	$82,883
2024	2019	COLLEGE OF WILLIAM AND MARY	1314 S MOUNT VERNON AVE	WILLIAMSBURG	VA	23185	JAMES CITY	USA	Biomedical Research and Research Training	000	2	2/21/2024	COMPETING CONTINUATION	-$82,883
														Subtotal = $0

Issue Date FY: 2023 ( Subtotal = $350,368 )
2023	2023	COLLEGE OF WILLIAM AND MARY	1314 S MOUNT VERNON AVE	WILLIAMSBURG	VA	23185	JAMES CITY	USA	Biomedical Research and Research Training	000	3	9/15/2023	COMPETING CONTINUATION	$350,368
														Subtotal = $350,368

Issue Date FY: 2019 ( Subtotal = $342,486 )
2019	2019	COLLEGE OF WILLIAM & MARY, THE	261 RICHMOND RD	WILLIAMSBURG	VA	23185	JAMES CITY	USA	Biomedical Research and Research Training	001	2	6/25/2019	COMPETING CONTINUATION	$342,486
2019	2014	COLLEGE OF WILLIAM & MARY, THE	261 RICHMOND RD	WILLIAMSBURG	VA	23185	JAMES CITY	USA	Biomedical Research and Research Training	000	1	6/21/2019	NEW	$0
														Subtotal = $342,486

Issue Date FY: 2018 ( Subtotal = $0 )
2018	2014	COLLEGE OF WILLIAM & MARY, THE	261 RICHMOND RD	WILLIAMSBURG	VA	23185	JAMES CITY	USA	Biomedical Research and Research Training	000	1	8/2/2018	NEW	$0
														Subtotal = $0

Issue Date FY: 2014 ( Subtotal = $294,000 )
2014	2014	COLLEGE OF WILLIAM & MARY	P.O. BOX 8795	WILLIAMSBURG	VA	23187	WILLIAMSBURG CITY	USA	Biomedical Research and Research Training	000	1	7/25/2014	NEW	$294,000
														Subtotal = $294,000

Grand Total All Awards = $986,854

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New methods to prepare 1,4-oxazin-2-ones and applications in the construction of polysubstituted pyridines

Award Number: R15GM107702

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: 09/01/2014

PERIOD OF PERFORMANCE END DATE: 08/31/2026

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