A novel one-pot base-promoted insertion of indolyl 2-alkynes into a C-C single bond of 1,3-diketones, followed by intramolecular aldol reaction and dehydrative aromatization is described. This reaction cascade leads to the construction of 2-indolyl phenols involving the formation of the C1-C2 and C3-C4 bonds of phenols resulting from the formal insertion process with a good substrate scope. Further, these bifunctional compounds were used in a novel arylative annulation in the presence of Grignard reagents to provide chromeno-indole frameworks.

A domino propargylation/furanylation (intramolecular exo-dig-cyclization)/benzannulation reaction of 2,4-diyn-1-ols with 1,3-dicarbonyl compounds has been developed for the first time. This provides a novel and effective method for the preparation of aryl/heteroaryl-fused benzofurans from easily accessible starting materials in a single step. The methodology was extended to pyrrolyl-benzannulation to obtain aryl/heteroaryl-fused indoles. Further, application of this approach in the synthesis of eustifoline D and dictyodendrin structural frameworks has been demonstrated.

An efficient acid-catalyzed propargylation/aza-annulation sequence was developed under metal-free reaction conditions, thus leading to a one-pot synthesis of a variety of substituted β-carbolines starting from propargylic alcohols and indole 2-carbonyls. This versatile strategy was further extended to the synthesis of 5-azaindoles and 5-azabenzothiazoles. Optical properties suggested that manipulation of electron donor and acceptor moieties on β-carbolines has an impact on their ground and excited state electronic behavior. This leads to blue or green emission and should facilitate the development of organic light emitting diodes (OLEDs). Electrochemical and stability studies revealed that 4a-6 shows ease of redox activity and photostability during illumination.

ChemInformVolume 33, Issue 45 p. 204-204 Natural Products Synthesis and Antiaggregant Properties of New Analogues of Polyunsaturated Fatty Acid Metabolites with Naphthalene of Quinoline Cores. Ali Hachem, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorYves Le Floc'h, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorRene Gree, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorChiara Cerletti, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorYves Rolland, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorSerge Simonet, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorTony Verbeuren, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this author Ali Hachem, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorYves Le Floc'h, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorRene Gree, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorChiara Cerletti, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorYves Rolland, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorSerge Simonet, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this authorTony Verbeuren, Lab. Synth. Act. Biomol., CNRS, Ec. Natl. Super. Chim., F-35700 Rennes, Fr.Search for more papers by this author First published: 19 May 2010 https://doi.org/10.1002/chin.200245204Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume33, Issue45November 12, 2002Pages 204-204 RelatedInformation

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The [4+3] cycloaddition reaction between alkyloxycarbonyl-substituted pyrroles and alpha,alpha'-dibromo ketones in the presence of diethylzinc has been extended to a wide range of substrates. The functionalization of the resulting tropanes has been studied. It is demonstrated that such tropanes represent potentially useful scaffolds.

The introduction of fluorine into organic molecules is an important tool in modifying their physical, chemical and biological properties. This review briefly presents the different approaches which can be used for selective monofluorination. The strategies that we have developed for fluorination vicinal to unsaturated systems, paying attention to the regio-and stereo-control during the fluorination step are then discussed in detail. From these studies, two promising approaches emerge : the first employs transition metal complexes; the second uses tailor made fluorinated key building blocks. Some applications to the preparation of natural product analogues are also mentioned.

Tetrahydropyridines 4a, 4b, 4c and pyridines 7a, 7b, 7c, 9a, 9b, 9c were synthesized by a [4 + 2] cycloaddition between 1,4-bis aryl-2-aza-1,3-butadienes and electron-poor dienophiles. Dimeric cycloadducts 6a, 6b, 6c, were also isolated indicating a competition between the expected Hetero Diels-Alder and a dimerization process.

Dithioester 10 was synthesized in 6 steps from tricarbonyl(diene)iron complex 3. Compound 10 is not only a key intermediate for the synthesis of methyl lipoate (13) but could also be of interest for the preparation of various labelled compounds and structural analogues.

New chiral rhenium complexes of allylic, homoallylic and propargylic alcohols have been prepared and their reactivity versus various reagents has been studied. Starting from the allyl alcohol complex, a multistep sequence involving a chemoselective oxidation, a Wittig reaction and a reduction led without bond-shift to conjugated dienone and dienol. The complexed allyl acetate, prepared by reaction of acetic anhydride on the complexed allyl alcohol reacted with sodium dimethylmalonate in a diastereoselective fashion.

Reaction of DAST with secondary alcohols vicinal to an arene Cr(CO)3 unit gives with very high exo stereoselectivity the corresponding fluorides; the stereochemistry of the reaction appears to be exclusively controlled by the organometallic moiety.

AbstractThe fumaraldehyde monoacetal (I) is oxidized with sodium chlorite to form the fumaraldehydic acid acetal (II) which is esterified with the chiral alcohols (III).

A short synthesis of the monodimethylacetal of fumaraldehydic acid 3 and the corresponding chiral esters 4 and 5 is reported. The key step is the oxidation of the fumaraldehyde monodimethylacetal 2.