Structure determination, correction, and disproof of marine macrolide natural products by chemical synthesis

Fuwa, Haruhiko

doi:10.1039/d1qo00481f

Cited by 21 publications

(8 citation statements)

References 185 publications

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“…NMR spectroscopy can equally be ambiguous for certain stereoclusters/conformations or complicated by overlapping signals in more complex natural products, rendering the extraction of coupling constants or nOes highly challenging and ultimately not definitive. This uncertainty provides a significant obstacle for synthesis and applications …”

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confidence: 99%

Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

et al. 2021

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The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens . Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We report a synthesis of the C1–C27 fragment of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence analysis as a powerful tool for stereochemical assignment of complex polyketide natural products.

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confidence: 99%

Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

et al. 2021

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“…It has helped to clarify the structure of some intriguing compounds, and to obtain higher amounts of them in order to perform proper biological studies. Total synthesis is still a crucial tool, as even with today's advanced NMR techniques, misassignment of the structure of biologically relevant macrolides is a common issue [1].…”

Section: Introductionmentioning

confidence: 99%

The Tetrahydrofuran Motif in Polyketide Marine Drugs

et al. 2022

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Oxygen heterocycles are units that are abundant in a great number of marine natural products. Among them, marine polyketides containing tetrahydrofuran rings have attracted great attention within the scientific community due to their challenging structures and promising biological activities. An overview of the most important marine tetrahydrofuran polyketides, with a focused discussion on their isolation, structure determination, approaches to their total synthesis, and biological studies is provided.

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“…Fortunately, the great contribution of chemists in the field of total synthesis and asymmetric catalysis over the last decades has had countless benefits. On one hand, even though nuclear magnetic resonance (NMR) techniques are very powerful tools, in some cases, the characterization of complex molecules can be difficult, leading to misassignments [ 5 ]. Fortunately, total synthesis has emerged as a—somewhat—costly but effective tool for the determination of the absolute configuration of marine metabolites.…”

Section: Introductionmentioning

confidence: 99%

The Tetrahydrofuran Motif in Marine Lipids and Terpenes

et al. 2022

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Heterocycles are particularly common moieties within marine natural products. Specifically, tetrahydrofuranyl rings are present in a variety of compounds which present complex structures and interesting biological activities. Focusing on terpenoids, a high number of tetrahydrofuran-containing metabolites have been isolated during the last decades. They show promising biological activities, making them potential leads for novel antibiotics, antikinetoplastid drugs, amoebicidal substances, or anticancer drugs. Thus, they have attracted the attention of the synthetics community and numerous approaches to their total syntheses have appeared. Here, we offer the reader an overview of marine-derived terpenoids and related compounds, their isolation, structure determination, and a special focus on their total syntheses and biological profiles.

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Structure determination, correction, and disproof of marine macrolide natural products by chemical synthesis

Abstract: Integration of chemical synthesis, NMR spectroscopy, and various analytical means is key to success in the structure elucidation of stereochemically complex marine macrolide natural products.

Cited by 21 publications

References 185 publications

Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

The Tetrahydrofuran Motif in Polyketide Marine Drugs

The Tetrahydrofuran Motif in Marine Lipids and Terpenes

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