61589-86-4Relevant academic research and scientific papers
Approach to the core structure of the polycyclic alkaloid palhinine A
Gaugele, Dominik,Maier, Martin E.
supporting information, p. 955 - 958 (2013/07/05)
A synthesis of the tricyclic partly substituted core structure of palhinine A was achieved. To reach the bicyclo[2.2.2]octane motif a domino Michael reaction was employed as a key step. After Arndt-Eistert homologation and intramolecular aldol reaction the isotwistane core could be obtained after simple functional-group manipulations. Georg Thieme Verlag Stuttgart . New York.
Synthesis of oxaspirannic building blocks by regioselective Nitroso-Diels-Alder reactions
Sancibrao, Pierre,Gori, Didier,Kouklovsky, Cyrille,Vincent, Guillaume
supporting information, p. 5557 - 5560 (2013/06/26)
Spirocyclic structures: Nitroso-Diels-Alder reactions of 1,3-disubstituted cyclohexadienes were found to be regiodivergent, depending on the nitroso derivative used. Cycloaddition with Wightman's chloronitroso derivative was totally regio- and stereoselec
A stereoselective, Sm(ii)-mediated approach to decorated cis-hydrindanes: Synthetic studies on faurinone and pleuromutilin
Findley, Thomas J. K.,Sucunza, David,Miller, Laura C.,Helm, Matthew D.,Helliwell, Madeleine,Davies, David T.,Procter, David J.
scheme or table, p. 2433 - 2451 (2011/05/06)
The cis-hydrindane motif is found in a number of natural products that display important biological activity. A flexible, stereoselective approach to the framework has been developed that features highly diastereoselective, SmI2-mediated cyclisations. The strategy has been exploited in the first synthesis of the proposed structure of faurinone and an approach to the skeleton of the antibacterial natural product, pleuromutilin.
A flexible, stereoselective approach to the decorated cis-hydrindane skeleton: Synthesis of the proposed structure of faurinone
Findley, Thomas J. K.,Sucunza, David,Miller, Laura C.,Davies, David T.,Procter, David J.
supporting information; experimental part, p. 6862 - 6865 (2009/07/18)
A flexible, stereoselective approach to the cis-hydrindane motif found in a number of biologically active natural products that utilizes highly diastereoselective SmI2-mediated cyclizations of aldehyde and halide substrates was demonstrated. Aldehydes were prepared to investigate the stereoselectivity of the proposed SmI2-mediated construction of the cis-hydrindane system. Treatment of aldehydes with SmI2 in THF and tBuOH resulted in successful cyclization and construction of three contiguous stereocenters. This cyclization proceeds through reduction of the aldehyde and addition of the resulting ketyl-radical anion to the alkene through anti-transition structure to give samarium (III) enolates. It was observed that SmI2-mediated halide-alkene cyclizations provide an easy alternative for the synthesis of less oxygenated targets.
Palladium-catalyzed synthesis of cephalotaxine analogues
Tietze, Lutz F.,Schirok, Hartmut,Woehrmann, Michael
, p. 510 - 518 (2007/10/03)
The synthesis of cephalotaxine ring analogues 10 was achieved by two successive intramolecular palladium-catalyzed reactions of 12 via 11, namely an allylic amination and a Heck reaction. The substrates 12 were obtained by alkylation of primary amines 13 with tosylates 14.
Alkoxides as Nucleophiles in (?-Allyl)palladium Chemistry. Synthetic and Mechanistic Studies
Stanton, Susan A.,Felman, Steven W.,Parkhurst, Carol S.,Godleski, Stephen A.
, p. 1964 - 1969 (2007/10/02)
A new methodology for the use of alkoxides as nucleophiles in (?-allyl)palladium chemistry has been developed.In this process an allylic alcohol serves as the precursor to the ?-allyl complex and a triethylsilyl (TES) ether as precursor to the alkoxide nucleophile.By using Pd(PPh3)4 in CCl4, PPh3Cl+CCl3- is generated transposing the ROH into an oxyphosphonium group, R-O-P+Ph3, and liberating Cl-.The Cl deprotects the TES ether, providing the nucleophile in situ.Application of this reaction to the preparation of a variety of furans is discussed.This process was determined to proceed with overall predominant retention of configuration.Mechanistic studies suggest a small energy difference between attack by alkoxide on the allyl ligand of the intermediate complex and attack on the metal, followed by reductive elimination.
Intramolecular Photoaddition of Terminal Allenes to Conjugated Cyclohexenones
Becker, Dan,Harel, Zvi,Nagler, Meshulam,Gillon, Arie
, p. 3297 - 3306 (2007/10/02)
Terminal allenes linked to cyclohexenones by hydrocarbon chains were synthesized and irradiated with UV ligth.It was found that cycloaddition occurs regiospecifically in high yield.The adducts were oxidized by ozone to 1,3-diketones which underwen
Palladium-Catalyzed Preparation of Carbon and Oxygen Spirocycles
Godleski, Stephen A.,Valpey, Richard S.
, p. 381 - 383 (2007/10/02)
A variety of substituted spiroundecene and spirodecene systems have been prepared by utilizing ?-allylpalladium chemistry in the key ring-forming step.
PALLADIUM ASSISTED SYNTHESIS OF 1-AZASPIROCYCLES
Godleski, Stephen A.,Meinhart, James D.,Miller, David J.,Wallendael, Shawn Van
, p. 2247 - 2250 (2007/10/02)
A facile, general route to 1-azaspirocycles utilizing a ?-allyl palladium complex in the key cyclization step has been developed.
