Concise total synthesis of (+/-)-aspidospermidine and computational study: FT-IR, NMR, NBO, NLO, FMO, MEP diagrams

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dc.authorid0000-0002-2819-3612
dc.authorid0000-0001-7649-9168
dc.authorscopusid36447801100
dc.authorscopusid6507868758
dc.authorwosidSerdaroğlu, Goncagül/I-6780-2016
dc.authorwosiduludag, Nesimi/AAB-1353-2020
dc.contributor.authorSerdaroğlu, Goncagül
dc.contributor.authorUludağ, Nesimi
dc.date.accessioned2022-05-11T14:30:58Z
dc.date.available2022-05-11T14:30:58Z
dc.date.issued2018
dc.departmentFakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.description.abstractAspidospermidine is a member of the compound class known as aspidospermaten-type alkaloids. Aspidospermidine is among the most highly sought aspidosperma alkaloid targets because it comprises the basic skeletal features of this family of natural products, particularly the complex and characteristic pentacyclic ABCDE framework. In this study, we used a new strategy developed to synthesize (+/-)aspidospermidine. The key steps involve a novel cyclization in a single step through an indoline substructure, leading to a versatile pentacyclic intermediate. The power of this concept has been demonstrated through the expedient, total syntheses of well-known alkaloid natural products including limaspermidine, vincadifformine, minovincine and cylindrocarine. Additionally, the PES scan has been performed to determine the stable conformers of the aspidospermidine compound at B3LYP/6-31G(d,p) level of theory in the gas phase and the stable conformers have been used to further analyses. The H-1 and C-1 NMR chemical shifts of the aspidospermidine compound have been observed by NMR spectroscopy and compared with the simulated by the GIAO (Gauge-Independent Atomic Orbital) approach. The vibrational modes determined by the FT-IR spectroscopy has been compared to the simulated vibrational modes of the aspidospermidine. The NBO analysis has been employed to elucidate the important intramolecular interactions causing the molecular stability and the optical properties of the aspidospermidine have been investigated by NLO analysis. The FMO analysis and MEP diagrams have been used to predict the physicochemical and quantum chemical properties being important to explore the chemical reactivity behavior of the aspidospermidine. (C) 2018 Elsevier B.V. All rights reserved.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [112T503]; Cumhuriyet University scientific research projects departmentCumhuriyet University [CUBAP: EGT-072]
dc.description.sponsorshipWe are grateful to Scientific and Technological Research Council of Turkey (TUBITAK Project No.112T503) for financial support and by the Cumhuriyet University scientific research projects department (Project No: CUBAP: EGT-072). All calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).
dc.identifier.doi10.1016/j.molstruc.2018.04.050
dc.identifier.endpage303
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85047443633
dc.identifier.scopusqualityQ2
dc.identifier.startpage286
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2018.04.050
dc.identifier.urihttps://hdl.handle.net/20.500.11776/7262
dc.identifier.volume1166
dc.identifier.wosWOS:000434005500032
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorUludağ, Nesimi
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectAspidospermidine
dc.subjectFT-IR
dc.subjectNMR
dc.subjectNBO
dc.subjectNLO
dc.subjectMolecular Docking
dc.subjectHomo-Lumo
dc.subjectKinetic Stability
dc.subjectDft
dc.subjectRaman
dc.subjectUv
dc.subjectAlkaloids
dc.subjectFramework
dc.subjectAspidospermidine
dc.subjectQuebrachamine
dc.titleConcise total synthesis of (+/-)-aspidospermidine and computational study: FT-IR, NMR, NBO, NLO, FMO, MEP diagrams
dc.typeArticle

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