Efficient Synthesis of 9- and 13-Oxo Leucomycin Derivatives Using Hypervalent Iodine Reagents in Solution and on Solid Support

Zöllner, Tina; Gebhardt, Peter; Beckert, Rainer; Hertweck, Christian

doi:10.1021/np049728+

Cited by 8 publications

(4 citation statements)

References 22 publications

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“…In particular, while a moderate rate enhancement was observed for the IBX amide resins with a short spacer 14) and longer spacer (w-AUA, 16), in the case of the IBX amide resin with the e-ACA spacer (15) the conver-sion was increased significantly from 17% to 63% after 12 hours of reaction. Thus, it was confirmed that the observed spacer effects were consistent with the hypothesis that the accessibility of the IBX amide toward decan-1-ol was an important factor in increasing the reaction rate.…”

Section: Biographical Sketchesmentioning

confidence: 98%

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Solid-Supported Reagents and Catch-and-Release Techniques in Organic Synthesis

Solinas¹,

Taddei

2007

Synthesis

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The use of polymer-supported reagents, catalysts and scavengers (and their appropriate combinations) represents a powerful approach for the synthesis of organic compounds, using both traditional and parallel solution-phase methodologies, and it has been of great interest in recent years, especially in the field of pharmaceutical research. Polymer-supported synthesis circumvents the need to bind the substrate to a solid support, and thereby allows for the reactions to be monitored with familiar analytical techniques. The purpose of this publication is to review the recent synthetic transformations (from 2001) carried out with solid-supported reagents, including the catch-and-release techniques, which represent a hybrid approach in between scavenging and solid-phase synthesis.

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Section: Biographical Sketchesmentioning

confidence: 98%

“…Polymer-supported 2-iodoxybenzoic acid reagents have been used in the development of an efficient procedure 14 for the highly selective oxidation of leucomycines to the corresponding 16-membered 9-oxo and 13-oxo macrolides. Polymer-bound IBX oxidants show clear advantages over the previously employed manganese dioxide.…”

Section: Biographical Sketchesmentioning

confidence: 99%

Solid-Supported Reagents and Catch-and-Release Techniques in Organic Synthesis

Solinas¹,

Taddei

2007

Synthesis

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“…132 Later, Ōmura et al conducted an extensive investigation on the structure and anti-microbial activity of several components of the leucomycin complex, leucomycins A1-9, U and V. [133][134][135][136][137][138][139] Different groups reported structural modifications to members of the leucomycin family in order to identify the moieties responsible for binding to the microbial ribosomes and therefore antibacterial activity. [140][141][142][143][144][145][146][147][148] Examples of modification and derivatization of the 16-membered macrolide antibiotics, in particular leucomycin and its analogs, have been reported in the literature. However, the structural changes consisted mostly in the acetylation or oxidation of the hydroxyl groups or the reduction of the aldehyde functionality and only a few examples dealt with the modification of the diene unit.…”

Section: Leucomycinmentioning

confidence: 99%

Nitroso Diels–Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products

Carosso

Miller

2014

Org. Biomol. Chem.

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This review describes the use of nitroso Diels-Alder reactions for the functionalization of complex diene-containing natural products in order to generate libraries of compounds with potential biological activity. The application of this methodology to the structural modification of a series of natural products (thebaine, steroidal dienes, rapamycin, leucomycin, colchicine, isocolchicine and piperine) is discussed using relevant examples from the literature from 1973 onwards. The biological activity of the resulting compounds is also discussed. Additional comments are provided that evaluate the methodology as a useful tool in organic, bioorganic and medicinal chemistry.

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“…A three-step preparation of a polymer-supported iodoxybenzoic acid (PSIBX) reagent from poly(p-methyl styrene) has been reported and it was used for the efficient oxidation of a series of alcohols to the corresponding aldehydes [19]. An efficient procedure for the highly selective oxidation of leucomycines to the corresponding 16-membered 9-and 13-oxomacrolides using hypervalent iodine reagents in solution and on solid support has been reported [20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization of Cellulose Grafted N-Oxide Reagent and Its Application in Oxidation of Alkyl/Aryl Halides

Kaur¹,

Dhiman²

2011

IJOC

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Oxidation of aliphatic and aromatic halides by N-oxide functionalities supported on 4-vinyl pyridine, (4-VP), grafted cellulose is reported in the present manuscript. Synthesis of graft copolymer of cellulose and poly 4-vinyl pyridine, poly(4-VP), has been carried out using ceric ions as redox initiator. Post-grafting treatment of CellO-g-poly(4-VP) with 30% H 2 O 2 in acetic acid gives Cellulose-g-poly(4-VP) N-oxide, the polymeric supported oxidizing reagent. The polymeric support, CellO-g-poly(4-VP) N-oxide, has been used for oxidation of different alkyl/aryl halide such as 1-bromo-3-methyl butane, 2-bromo propane, 1-bromo heptane and benzyl chloride. The polymeric reagent was characterized by IR and thermo-gravimetric analysis. The oxidized products were characterized by FTIR and H 1 NMR spectral methods. The reagent was reused for the oxidation of a fresh alkyl/aryl halides and it was observed that the polymeric reagent oxidizes the compounds successfully but with little lower product yield.

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Efficient Synthesis of 9- and 13-Oxo Leucomycin Derivatives Using Hypervalent Iodine Reagents in Solution and on Solid Support

Cited by 8 publications

References 22 publications

Solid-Supported Reagents and Catch-and-Release Techniques in Organic Synthesis

Solid-Supported Reagents and Catch-and-Release Techniques in Organic Synthesis

Nitroso Diels–Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products

Synthesis, Characterization of Cellulose Grafted N-Oxide Reagent and Its Application in Oxidation of Alkyl/Aryl Halides

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