The Curtius Reaction

Smith, Peter A.

doi:10.1002/0471264180.or003.09

Cited by 20 publications

(11 citation statements)

References 315 publications

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“…The Curtius rearrangement is a classic method for stereoselective formation of C–N bonds involving degradation of acyl azides into isocyanates, which could be trapped with various nucleophiles. , Starting from readily available chiral carboxylic acids or their derivatives, acyl azides generated under mild conditions undergo a facile rearrangement with retention of configuration at the migrating carbon. Thus, it is not surprising that the Curtius rearrangement is used frequently in total synthesis.…”

Section: Nitrenoid Rearrangementsmentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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The main objective of this review is to provide a comprehensive survey of methods used for stereoselective construction of carbon-nitrogen bonds during the total synthesis of nitrogen-containing natural products that have appeared in the literature since 2000. The material is organized by specific reaction in order of decreasing number of applications in natural product synthesis. About 800 total syntheses of natural products with stereogenic carbon-nitrogen bonds described since 2000 have been reviewed.

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Section: Nitrenoid Rearrangementsmentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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“…Rhodamine was linked to mensacarcin using tetramethylrhodamine-5-carbonyl azide (TMRCA) following established protocols (35). Upon heating TMRCA to 80°C, the azide group undergoes a Curtius rearrangement to yield the isocyanide group, which instantly reacts with mensacarcin's hydroxyl groups to form the carbamate-linked conjugate (TMR-mensa) (36,37) (Fig. 7A).…”

Section: Rhodamine-labeled Mensacarcin Induces Apoptotic Cell Death Imentioning

confidence: 99%

The natural product mensacarcin induces mitochondrial toxicity and apoptosis in melanoma cells

Plitzko¹,

Kaweesa

Loesgen

2017

Journal of Biological Chemistry

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Mensacarcin is a highly oxygenated polyketide that was first isolated from soil-dwelling bacteria. It exhibits potent cytostatic properties (mean of 50% growth inhibition = 0.2 μm) in almost all cell lines of the National Cancer Institute (NCI)-60 cell line screen and relatively selective cytotoxicity against melanoma cells. Moreover, its low COMPARE correlations with known standard antitumor agents indicate a unique mechanism of action. Effective therapies for managing melanoma are limited, so we sought to investigate mensacarcin's unique cytostatic and cytotoxic effects and its mode of action. By assessing morphological and biochemical features, we demonstrated that mensacarcin activates caspase-3/7-dependent apoptotic pathways and induces cell death in melanoma cells. Upon mensacarcin exposure, SK-Mel-28 and SK-Mel-5 melanoma cells, which have the BRAF mutation associated with drug resistance, showed characteristic chromatin condensation as well as distinct poly(ADP-ribose)polymerase-1 cleavage. Flow cytometry identified a large population of apoptotic melanoma cells, and single-cell electrophoresis indicated that mensacarcin causes genetic instability, a hallmark of early apoptosis. To visualize mensacarcin's subcellular localization, we synthesized a fluorescent mensacarcin probe that retained activity. The natural product probe was localized to mitochondria within 20 min of treatment. Live-cell bioenergetic flux analysis confirmed that mensacarcin disturbs energy production and mitochondrial function rapidly. The subcellular localization of the fluorescently labeled mensacarcin together with its unusual metabolic effects in melanoma cells provide evidence that mensacarcin targets mitochondria. Mensacarcin's unique mode of action suggests that it may be a useful probe for examining energy metabolism, particularly in BRAF-mutant melanoma, and represent a promising lead for the development of new anticancer drugs.

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“…A/B type PU ( 6 ) can be obtained by Curtius rearrangement [ 51 , 62 , 63 , 64 , 65 , 66 , 67 , 68 ], thus, fatty acid derivatives such as ( ω -1) HFA represent potential A/B type monomers for the synthesis of PU [ 69 ]. By modification of model reactions [ 72 , 73 ], a reaction procedure comprising ( ω -1) HFA ( 2 ) → ( ω -1) HFA azide ( 5 ) → ( ω -1) HFA-based A/B PU ( 6 ) could be developed ( Figure 15 ).…”

Section: Resultsmentioning

confidence: 99%

“…Note that successive conversion with diisocyanates to high molecular weight PU requires two-fold OH termination, which can be accomplished, e.g., by initiation with or addition of suitable diols [ 55 , 61 ]. Additionally, the acid moiety of HFA can be converted to azide in order to accomplish Curtius rearrangement [ 62 ] yielding A/B type polyurethanes [ 51 , 63 , 64 , 65 , 66 , 67 , 68 ].…”

Section: Introductionmentioning

confidence: 99%

Sophorolipid-Based Oligomers as Polyol Components for Polyurethane Systems

et al. 2021

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Due to reasons of sustainability and conservation of resources, polyurethane (PU)-based systems with preferably neutral carbon footprints are in increased focus of research and development. The proper design and development of bio-based polyols are of particular interest since such polyols may have special property profiles that allow the novel products to enter new applications. Sophorolipids (SL) represent a bio-based toolbox for polyol building blocks to yield diverse chemical products. For a reasonable evaluation of the potential for PU chemistry, however, further investigations in terms of synthesis, derivatization, reproducibility, and reactivity towards isocyanates are required. It was demonstrated that SL can act as crosslinker or as plasticizer in PU systems depending on employed stoichiometry. (ω-1)-hydroxyl fatty acids can be derived from SL and converted successively to polyester polyols and PU. Additionally, (ω-1)-hydroxyl fatty acid azides can be prepared indirectly from SL and converted to A/B type PU by Curtius rearrangement.

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The Curtius Reaction

Cited by 20 publications

References 315 publications

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

The natural product mensacarcin induces mitochondrial toxicity and apoptosis in melanoma cells

Sophorolipid-Based Oligomers as Polyol Components for Polyurethane Systems

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