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ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTotal Synthesis of Oxacyclic Macrodiolide Natural ProductsEun Joo Kang and Eun LeeView Author Information Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Korea Cite this: Chem. Rev. 2005, 105, 12, 4348–4378Publication Date (Web):September 21, 2005Publication History Received1 March 2005Published online21 September 2005Published inissue 1 December 2005https://doi.org/10.1021/cr040629aCopyright © 2005 Ameri

Single-electron oxidation and α-deprotonation of tertiary anilines using Fe(phen)₃(PF₆)₃ afford α-aminoalkyl radicals, which can be coupled with electrophilic partners to afford various tetrahydroquinolines. Mechanistically, the Fe(phen)_<i>n</i>^2+/3+ catalytic cycle is maintained by O₂ or a TBHP oxidant, and the presence of the oxygen bound iron complex, Fe(III)-OO(H), was elucidated by electron paramagnetic resonance and electros

(+)-SCH 351448 (Na+ salt A) was synthesized employing ring-closing olefin metathesis reaction of an open diene diester intermediate for construction of the 28-membered macrodiolide structure. The open diene diester was prepared from the monomeric hydroxy carboxylic acid and two different olefin fragments. The monomeric hydroxy acid was synthesized via Julia-Julia coupling reaction of intermediates derived from the same olefinic fragments. Oxane units in these fragments were prepared by radical c

A novel selective nanoscale etching process that generated a well defined hollow nanostructure was developed by treating manganese oxide nanoparticles with a hydroxylamine solution. This selective etching process was used for exploiting a novel method of differentially functionalizing the internal surface of a hollow silica shell with a catalytically active Mn3O4 layer and creating a novel nanoreactor framework. The nanoreactor fabricated by the newly developed method catalyzed the cyanosilylati

Two of a kind: A new type of counterion-mediated syn-addition mechanism has been presented in gold-catalyzed enantioselective hydroamination reactions with [(R)-binap(AuOPNB)2] (OPNB=para-nitrobenzoate). A combination of both hydrogen bonding and the NAu interaction efficiently controlled the challenging enantioselectivity of allenes.

A range of tetrahydropyrans and piperidines were produced by Fe(III)-catalyzed intramolecular hydroalkoxylation and hydroamination reactions of allenes. Various Fe catalysts with different counterions were tested. Their activities toward allene and alkene activation depended sensitively on their counterion and reaction conditions. Mechanistic study of the reaction intermediates found a new reaction pattern involving the Fe catalysts and diene substrates.

The iron(III)-polypyridyl complex and its derivatives showed sufficient oxidizing potential to act as a one-electron oxidant, producing radical cations from olefins and promoting the efficient radical cation [2 + 2] and [2 + 4] cycloaddition reactions. Subsequent chain propagation afforded trisubstituted cyclobutane or cyclohexene derivatives, and this facile route enables the replacement of rare metals with sustainable, green, and inexpensive iron in radical cation cycloadditions.

Total synthesis of SCH 351448 was accomplished employing the ring-closing olefin metathesis reaction for the preparation of the 28-membered macrodiolide.

Green-light-driven Fe^III(btz)₃ photocatalysis for the radical cationic [4+2] cycloaddition of terminal styrenes and nucleophilic dienes has been investigated. The Fe-MIC (mesoionic carbene) complex forms a ligand-to-metal charge-transfer transition state with relatively high excited-state reduction potentials that can selectively oxidize terminal styrene derivatives. Unique multisubstituted cyclohexenes and structurally complex biorelevant cyclohexenes were constructed, hig

N-Hetereocyclic carbenes (NHCs) were found to be efficient catalysts for the cyclization of propargylic alcohols and isocyanates. Domino cyclization reactions were carried out using isopropyl-substituted imidazolium salt as a precatalyst, and a wide range of substituted oxazolidinones were obtained in high yields.

An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO) 5 ] to generate radical species from alkyl iodides was achieved. A range of pyrrolidines, tetrahydrofurans, and carbocycles were synthesized via 5- exo cyclization reactions of alkyl radical intermediates generated by electron transfer from a system involving Fe(CO) 5, 1,10-phenanthroline, and diisopropylamine. Moreover, tandem addition reactions with Michael acceptors were also explored. Photophysical and electrochemical

Abstract A range of arylmethyl‐substituted pyrrolidines and tetrahydrofurans were produced by FeCl 2 ‐catalyzed tandem cyclization and cross‐coupling reactions of alkyl iodides and aryl Grignard reagents. The substituents on alkenes had a profound effect on the progress of the tandem reactions, with di‐ and tri‐substituted alkenes affording cyclized pyrrolidines. Several experimental results, such as cyclopropyl ring opening, the stereochemical outcome of the reaction with a secondary iodide sub

The use of multifunctional and sustainable Fe catalysts for the formation of cyclic carbonates from epoxides and carbon dioxide at 80 °C and 3 bar pressure is presented. The optimal catalyst possesses a halide counteranion and a hydrogen bond donor to activate the epoxide for ring opening, affording a single-component, cocatalyst-free catalytic system.

The intramolecular didehydro-Diels-Alder reaction of styrene-ynes was catalyzed by Fe(II) and Fe(III) to produce various naphthalene derivatives under microwave heating conditions. Mechanistic calculations found that the Fe(II) catalyst activates the styrenyl diene in an inverse-electron-demand Diels-Alder reaction, and the consecutive dehydrogenation reaction can be promoted by either Fe(II)-catalyzed direct dehydrogenation or an Fe(III)-catalyzed rearomatization/dehydrogenation pathway.

Abstract Single electron oxidation of electron‐rich alkenes using the iron(III)‐phenanthroline complex produced electrophilic alkene radical cations, which promoted efficient radical cation [2+1] cycloaddition reactions with diazo compounds. Subsequent chain propagation afforded tri‐ and tetra‐substituted cyclopropanes. This methodology was also expanded to [3+2] cycloaddition reactions with vinyl diazoesters, validating this sustainable, first‐row transition metal iron system for the single ele