Benzannulation and Hydrocarboxylation Methods for the Synthesis of a Neopentylene-Fused Analogue of Ibuprofen.

A C Martin, Jessica A Rogers, Paratchata Batsomboon, Alec E Morrison, Ron R Ramsubhag, Brian V Popp, Gregory B Dudley

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Article in ACS omega, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

7 authors.

A C MartinC. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26505, United States.

Jessica A RogersC. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26505, United States.

Paratchata BatsomboonC. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26505, United States.ORCID https://orcid.org/0000-0001-6470-9084

Alec E MorrisonDepartment of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States.

Ron R RamsubhagDepartment of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States.

Brian V PoppC. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26505, United States.ORCID https://orcid.org/0000-0001-6367-1168

Gregory B DudleyC. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26505, United States.ORCID https://orcid.org/0000-0001-6133-3747

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Neopentylene ring fusions (ring-fused 4,4-dimethylcyclopentane polycycles) are found in many natural products, but they are largely absent from synthetic compound libraries and focused medicinal chemistry research. Here is reported a synthetic approach to one of the few non-natural product-based target compounds from medicinal chemistry that includes a neopentylene ring fusion: an analogue of ibuprofen referred to herein as "neoprofen". The approach features ring-opening fragmentation reactions of dimedone derivatives coupled with transition metal-catalyzed benzannulation and hydrocarboxylation methods.

Identifiers

PMID34778682

DOI10.1021/acsomega.1c04943

PMCPMC8582271

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LicenceCC BY-NC-ND

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.