Total Synthesis of Aquatolide

Saya, Jordy M.; Vos, Klaas; Kleinnijenhuis, Roel A.; Maarseveen, Jan H. van; Ingemann, Steen; Hiemstra, Henk

doi:10.1021/acs.orglett.5b01888

Cited by 50 publications

(53 citation statements)

References 18 publications

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“…The structure 153 proposed by Tantillo and co-workers 77 was eventually prepared by Hiemstra and co-workers 77 featuring an intramolecular [2 + 2]-photocycloaddition between an allene and an α,β-unsaturated δ-lactone as the key step to construct its tricyclic core (Scheme 20). 79 The synthesis started with a Ti(O i Pr) 4 promoted cross aldol involving isobutyraldehyde (154) and propargylic aldehyde which required conversion of the product into the corresponding dimetylacetal 155. Esterification of 155 provided the requisite phosphonate 156 and paved the way for the intramolecular Horner-Wadsworth- Emmons reaction which afforded the corresponding α,β-unsaturated-δ-lactone which was finally converted to allenic lactone 157.…”

Section: Aquatolidementioning

confidence: 99%

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Della‐Felice¹,

Pilli²,

Sarotti³

2018

J. Braz. Chem. Soc.

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Quantum chemical calculations of nuclear magnetic resonance (NMR) shifts and coupling constants have been extensively employed in recent years mainly to facilitate structural elucidation of organic molecules. When the results of such calculations are used to determine the most likely structure of a natural product in advance, guiding the subsequent synthetic work, the term "computer-guided synthesis" could be coined. This review article describes the most relevant examples from recent literature, highlighting the scope and limitations of this merged computational/experimental approach as well.

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Section: Aquatolidementioning

confidence: 99%

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Della‐Felice¹,

Pilli²,

Sarotti³

2018

J. Braz. Chem. Soc.

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“…1, 2 In the course of this work, the total synthesis of aquatolide was published. 6 Again, the authors provided the original FID, from which we could demonstrate the rapid dereplication of the isolated natural product vs. the synthesized compound. The resulting report 1 demonstrates the power of shared HNMR FIDs and adequate tabular description for the promotion of accurate structural elucidation and reliable dereplication.…”

Section: B Fids Foster Reproducibility and Integritymentioning

confidence: 99%

Dissemination of original NMR data enhances reproducibility and integrity in chemical research

et al. 2016

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The notion of data transparency is gaining a strong awareness among the scientific community. The availability of raw data is actually regarded as a fundamental way to advance science by promoting both integrity and reproducibility of research outcomes. Particularly, in the field of natural product and chemical research, NMR spectroscopy is a fundamental tool for structural elucidation and quantification (qNMR). As such, the accessibility of original NMR data, i.e., Free Induction Decays (FIDs), fosters transparency in chemical research and optimizes both peer review and reproducibility of reports by offering the fundamental tools to perform efficient structural verification. Although original NMR data are known to contain a wealth of information, they are rarely accessible along with published data. This Viewpoint discusses the relevance of the availability of orginal NMR data as part of Good Research Practices not only to promote structural correctness, but also to enhance traceability and reproducibility of both chemical and biological results.

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“…and Ito et al. recently reported the syntheses of aquatolide and naupliolide by constructing the challenging small rings at the beginning of their respective sequences …”

Section: Introductionmentioning

confidence: 99%

Ruthenium-Catalyzed Metathesis Cascade Reactions in Natural Products Synthesis

Han

2016

Chem. Rec.

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In this account, we provide a brief summary of recent developments in ruthenium-catalyzed metathesis cascade reactions towards the total synthesis of natural products. We also highlight recent progress from our own laboratory regarding the synthesis of securinega alkaloids and humulanolides, which has resulted in the development of novel ruthenium-catalyzed metathesis cascade reactions. Inspired and guided by the pioneering and elegant research conducted in this area, we developed a regio-controlled relay dienyne metathesis cascade reaction and a cyclobutene-promoted RCM/ROM/RCM cascade reaction for the synthesis of securinega alkaloids and humulanolides, respectively.

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Total Synthesis of Aquatolide

Cited by 50 publications

References 18 publications

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Dissemination of original NMR data enhances reproducibility and integrity in chemical research

Ruthenium-Catalyzed Metathesis Cascade Reactions in Natural Products Synthesis

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