Four Routes to 3-(3-Methoxy-1,3-dioxopropyl)pyrrole, a Core Motif of Rings C and E in Photosynthetic Tetrapyrroles.

Khiem Chau Nguyen, Anh Thu Nguyen Tran, Pengzhi Wang, Shaofei Zhang, Zhiyuan Wu, Masahiko Taniguchi, Jonathan S Lindsey

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Article in Molecules (Basel, Switzerland), 2023. 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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7 authors.

Khiem Chau NguyenDepartment of Chemistry, North Carolina State University, Raleigh, NC 27695, USA.

Anh Thu Nguyen TranDepartment of Chemistry, North Carolina State University, Raleigh, NC 27695, USA.

Pengzhi WangDepartment of Chemistry, North Carolina State University, Raleigh, NC 27695, USA.

Shaofei ZhangDepartment of Chemistry, North Carolina State University, Raleigh, NC 27695, USA.

Zhiyuan WuDepartment of Chemistry, North Carolina State University, Raleigh, NC 27695, USA.ORCID 0000-0002-4330-1271

Masahiko TaniguchiDepartment of Chemistry, North Carolina State University, Raleigh, NC 27695, USA.ORCID 0000-0003-3735-0584

Jonathan S LindseyDepartment of Chemistry, North Carolina State University, Raleigh, NC 27695, USA.ORCID 0000-0002-4872-2040

Funding

National Science Foundation CHE-1760839National Science Foundation CHE-2054497

6 · The paper itself

Abstract

The photosynthetic tetrapyrroles share a common structural feature comprised of a β-ketoester motif embedded in an exocyclic ring (ring E). As part of a total synthesis program aimed at preparing native structures and analogues, 3-(3-methoxy-1,3-dioxopropyl)pyrrole was sought. The pyrrole is a precursor to analogues of ring C and the external framework of ring E. Four routes were developed. Routes 1-3 entail a Pd-mediated coupling process of a 3-iodopyrrole with potassium methyl malonate, whereas route 4 relies on electrophilic substitution of TIPS-pyrrole with methyl malonyl chloride. Together, the four routes afford considerable latitude. A long-term objective is to gain the capacity to create chlorophylls and bacteriochlorophylls and analogues thereof by facile de novo means for diverse studies across the photosynthetic sciences.

Indexed as

PyrrolesTetrapyrrolesBacteriochlorophyllsChlorophyllPhotosynthesisBacteriochlorophyllsChlorophyllPyrrolesTetrapyrrolesacylationbacteriochlorophyllBoc-pyrrolecarbonylationchlorophyllsynthesisTIPS-pyrroleβ-ketoester

Identifiers

PMID36770988

DOI10.3390/molecules28031323

PMCPMC9920783

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