Synthese totale du paratrifluoroacetamidophenyl-20 LTA4 (ester methylique)

Perrin, Patrick; Aubert, F.; Lellouche, Jean‐Paul; Beaucourt, J. P.

doi:10.1016/s0040-4039(00)85430-1

Cited by 12 publications

(1 citation statement)

References 5 publications

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“…The Grignard reagent 36 was derived from the corresponding bromide (generated from the THP ether of pent-4-yn-1-ol and 1,3-dibromopropane) [18] and was coupled with iodide 26 in the presence of Li 2 CuCl 4 catalyst to afford alkyne 37 (84% yield). Removal furnishing primary alcohol 52 in quantitative yield from compound 51.…”

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Total Synthesis and Biological Evaluation of Glycolipids Plakosides A, B and Their Analogs

Nicolaou

Zenke

2000

HCA

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Dedicated to Professor Albert Eschenmoser on the occasion of his 75th birthday for his outstanding contributions to organic and bioorganic chemistryThe total synthesis of plakosides A (1) and B (2), and their designed analogs 3 ± 10 was accomplished. The convergent strategy employed involved construction of the individual building blocks employing the Sharpless asymmetric dihydroxylation and the Charette asymmetric cyclopropanation reactions to introduce the desired configuration, followed by their couplings and final elaboration. Thus, key intermediates 12 ± 14 were prepared in their optically active forms and joined through a glycosidation reaction and amide-bond formation to yield the target molecules after appropriate elaboration and final deprotection. The synthesized compounds 1 ± 10 were evaluated for their immunosuppressive properties in vitro and found to be only modestly active.

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confidence: 99%

Total Synthesis and Biological Evaluation of Glycolipids Plakosides A, B and Their Analogs

Nicolaou

Zenke

2000

HCA

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Organocopper Reagents: Substitution, Conjugate Addition, Carbo/Metallocupration, and Other Reactions

1992

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Well over a decade ago, two reviews were contributed to the Organic Reactions series covering substitution and conjugate addition reactions in organocopper chemistry. Their appearance, which highlighted most of the early work in this field, served not only as a source of invaluable references to original literature reports, but also stimulated a vast number of subsequent studies on the properties and uses of organocopper complexes. The work cited in this chapter, which dates from ca. 1975, concerns in large measure uses of organocopper complexes originating from either catalytic or stoichiometric quantities of a copper(I) halide together with a Grignard (RMgX) or organolithium (RLi) reagent. These combinations form either neutral organocopper reagents RCu ( 1 ) or copper(I) monoanionic salts R 2 CuM (M = Li or MgX), commonly referred to as “lower‐order” species. The latter ate complexes with lithium as gegenion ( 2 ) are also known as “Gilman reagents” in recognition of their origins. Copper(I) cyanide is also an excellent precursor, affording homogeneous mixtures of lower order cyanocuprates RCu(CN)Li, ( 3 ), upon treatment with an equivalent of an organolithium. The strength of the CuCN linkage presumably accounts for direct cuprate formation with 1 equivalent of the organolithium, rather than the metathesis that occurs with copper(I) chloride, bromide, or iodide. While use of reagents ( 1 ), ( 2 ) and ( 3 ) alone can be aptly classified as broad‐based and intense, their importance has further encouraged extensive development of variations on these themes (i.e., their composition and reactivity profiles). Reagents ( 1–3 ) have been found to be unexpectedly compatible with certain electrophilic additives at low temperatures, which substantially alter their reactivity. Rather than forming ( 2 ) from 2 equivalents of the same RLi, different organolithiums can be utilized to give R T R R CuLi, ( 4 ), conserving potentially valuable RLi. This scenario raises the question of controlling the selectivity of transfer of the desired ligand R T rather than the anticipated residual (or “dummy”) group R R from copper to electrophilic carbon. Fortunately, many solutions to this problem now exist. Admixture of 2RLi (or R T Li + R R Li) with copper(I) cyanide proceeds beyond the stage of ( 3 ) to ultimately arrive at copper(I) dianionic complexes 5 , the so‐called “higher‐order” cyanocuprates. Undoubtedly it is the cyano ligand, with its π‐acidic nature, which enables copper to accept a third negatively charged ligand. Although reagents ( 5 ) do not yet share in all of the benefits offered by time in comparison with their lower‐order counterparts, they nicely complement prior art. Moreover, as with species ( 1–4 ), they continue to evolve, providing the synthetic community with alternatives for highly selective and efficient means of making key carbon–carbon bonds.

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Electrophilic Amination of Carbanions, Enolates, and Their Surrogates

Ciganek

2009

Organic Reactions

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This chapter deals with the formation of carbon‐nitrogen bonds by reaction of carbon nucleophiles with electrophilic aminating reagents. The former encompass aliphatic and aromatic carbanions, enolates and their surrogates such as enamines, enol esters, and enol ethers, as well as carbanions stabilized by cyano or sulfone groups or by phosphorus. A section entitled Reagents and Mechanisms lists the many aminating reagents available and discusses the mechanisms by which the more important ones react. Among the electrophiles discussed are halo amines, various hydroxylamine derivatives, oxaziridines, imines, oximes, diazonium salts, diazo compounds, azo compounds, and azides. The section on Scope and Limitations is organized by carbon nucleophiles and attempts to suggest the best reagents for each class. A number of electrophilic aminating reagents that have been omitted from the scope of this chapter are briefly discussed, with references to reviews, in the section on Comparison with Other Methods. Tables listing references to the preparation of the various aminating reagents are found in the section on Experimental Conditions. References to the conversion of non‐amine products into amines are also provided there. The literature is covered to the middle of 2007.

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Synthese totale du paratrifluoroacetamidophenyl-20 LTA4 (ester methylique)

Cited by 12 publications

References 5 publications

Total Synthesis and Biological Evaluation of Glycolipids Plakosides A, B and Their Analogs

Total Synthesis and Biological Evaluation of Glycolipids Plakosides A, B and Their Analogs

Organocopper Reagents: Substitution, Conjugate Addition, Carbo/Metallocupration, and Other Reactions

Electrophilic Amination of Carbanions, Enolates, and Their Surrogates

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