Theoretical Study on the Biosynthesis of the Mandapamates: Mechanistic Insights Using Density Functional Theory.

Di Wang, Gerald Pattenden, Kam Loon Fow, Michael J Stocks, Jonathan D Hirst, Bencan Tang

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Article in The Journal of organic chemistry, 2024. 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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6 authors.

Di WangDepartment of Chemical and Environmental Engineering, Nottingham Ningbo China Beacons of Excellence Research and Innovation Institute, Key Laboratory for Carbonaceous Waste Processing and Process Intensification Research of Zhejiang Province, the University of Nottingham Ningbo China, 199 Taikang East Road, Ningbo 315100, P. R. China.

Gerald PattendenSchool of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, U.K.

Kam Loon FowDepartment of Chemical and Environmental Engineering, Nottingham Ningbo China Beacons of Excellence Research and Innovation Institute, Key Laboratory for Carbonaceous Waste Processing and Process Intensification Research of Zhejiang Province, the University of Nottingham Ningbo China, 199 Taikang East Road, Ningbo 315100, P. R. China.ORCID 0000-0002-8165-9477

Michael J StocksNottingham University Biodiscovery Institute, School of Pharmacy, University of Nottingham, University Park, Nottingham NG7 2RD, U.K.ORCID 0000-0003-3046-137X

Jonathan D HirstSchool of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, U.K.ORCID 0000-0002-2726-0983

Bencan TangDepartment of Chemical and Environmental Engineering, Nottingham Ningbo China Beacons of Excellence Research and Innovation Institute, Key Laboratory for Carbonaceous Waste Processing and Process Intensification Research of Zhejiang Province, the University of Nottingham Ningbo China, 199 Taikang East Road, Ningbo 315100, P. R. China.ORCID 0000-0002-4301-2496

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Density functional theory (B3LYP-D3(BJ) and ωB97XD) calculations have been used to assess the stereochemical outcomes of the proposed transannular [4 + 2] cycloaddition pathway for the biosynthesis of mandapamate and isomandapamate from macrocyclic intermediates. Calculations reveal that the topological shift between macrocyclic conformers is vital in controlling the stereoselectivity of the downstream steps toward the isomeric mandapamates. A stepwise 4 + 2 type process is energetically favored over a concerted [4 + 2] pathway at room temperature, and is consistent with the stereochemistries found in the natural products.

Identifiers

PMID39248097

DOI10.1021/acs.joc.4c00859

PMCPMC11421023

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