The furan approach to oxygenated natural products. Total synthesis of (+)-KDO

Martin, Stephen F.; Zinke, Paul W.

doi:10.1021/jo00023a028

Cited by 64 publications

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“…Other examples were also studied, with similar results. The resultant products were converted in a few steps and with high optical purity into chiral furyl carbinols, which are useful precursors of bioactive products, such as the selective antifungal populacandin D ( Balachari and O’Doherty, 2000 ), or KDO, a vital component of the Gram-negative bacteria cell wall ( Martin and Zinke, 1991 ).…”

Section: Oxidative O -Radical Scission-addition Of...mentioning

confidence: 99%

“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles

et al. 2022

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Hypervalent iodine reagents have been applied in many metal-free, efficient synthesis of natural products and other bioactive compounds. In particular, treatment of alcohols, acetals and acids with hypervalent iodine reagents and iodine results in O-radicals that can undergo a β-scission reaction. Under these oxidative conditions, derivatives of amino acids, peptides or carbohydrates are converted into cationic intermediates, which can subsequently undergo inter- or intramolecular addition of nucleophiles. Most reported papers describe the addition of oxygen nucleophiles, but this review is focused on the addition of carbon, nitrogen and phosphorous nucleophiles. The resulting products (nucleoside and alkaloid analogs, unnatural amino acids, site-selectively modified peptides) are valuable intermediates or analogs of bioactive compounds.

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Section: Oxidative O -Radical Scission-addition Of...mentioning

confidence: 99%

“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles

et al. 2022

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“…Some oxygenated natural products that captured our interest included Prelog–Djerassi lactone, 2 3-deoxy- d -manno-2-octulosonic acid [(+)-KDO], 3 1-deoxycastanospermine, 4 tirandamycin A, 5 macbecin I, 6 herbimycin A, 7 and erythromycin B (Figure 1). 8,9 …”

Section: Synthesis Of Oxygenated Natural Productsmentioning

confidence: 99%

“…In the early days at The University of Texas, we were drawn to the challenges associated with developing short and efficient approaches to the synthesis of oxygenated natural products, including those having functionally and structurally complex frameworks. Some oxygenated natural products that captured our interest included Prelog–Djerassi lactone, 3-deoxy- d -manno-2-octulosonic acid [(+)-KDO], 1-deoxycastanospermine, tirandamycin A, macbecin I, herbimycin A, and erythromycin B (Figure ). , …”

Section: Synthesis Of Oxygenated Natural Productsmentioning

confidence: 99%

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Martin

2017

J. Org. Chem.

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Diverse structural types of natural products and their mimics have served as targets of opportunity in our laboratory to inspire the discovery and development of new methods and strategies to assemble polyfunctional and polycyclic molecular architectures. Furthermore, our efforts toward identifying novel compounds having useful biological properties led to the creation of new targets, many of which posed synthetic challenges that required the invention of new methodology. In this Perspective, selected examples of how we have exploited a diverse range of natural products and their mimics to create, explore, and solve a variety of problems in chemistry and biology will be discussed. The journey was not without its twists and turns, but the unexpected often led to new revelations and insights. Indeed, in our recent excursion into applications of synthetic organic chemistry to neuroscience, avoiding the more-traveled paths was richly rewarding.

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“…Enhanced chemoselectivity and very good functional group tolerance make the vanadium-catalyzed oxygenation a privileged method for the preparation of synthetically attractive pyranones; hence, it serves as a frequently used protocol not only in the total synthesis of highly complex glycosidic natural products such as KDO, spliceostatin A and the ipomoeassins (Scheme 30), [99][100][101] but also in strategies towards polyketidic macrolides, 102 polyethers 103 and terpenoic structures. 104,105 Similarly to the Sharpless epoxidation, the use of tartrate-modified titanium alkoxides instead of vanadyl acetylacetone allows for enantiodiscriminating oxygenative furan cleavage.…”

Section: Figure 1 Catalytic Species Observed By 51 V-nmr During the Rmentioning

confidence: 99%

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

2015

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Over the years, the oxidative ring enlargement of furfuryl alcohols, known as the Achmatowicz reaction, has been developed into a powerful and versatile synthetic tool for the preparation of 6-hydroxypyranones. This review provides a comprehensive collection of the various ways to perform Achmatowicz rearrangement reactions and explores the role of this ring-expansion process in contemporary organic synthesis. 1 Introduction 2 Classical Methods and Variants 3 Single-Electron-Transfer Oxidations 4 Metal-Catalyzed Ring Expansions 5 Photolytic Oxygenations 6 Enzymatic Transformations 7 Conclusions

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The furan approach to oxygenated natural products. Total synthesis of (+)-KDO

Cited by 64 publications

References 0 publications

“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles

“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles

Natural Products and Their Mimics as Targets of Opportunity for Discovery

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

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