Chiral Butenolides Research Articles

ChemInform Abstract: Asymmetric Synthesis of Dibenzylbutyrolactones (VIII) and Aryltetralin Lignan Lactones (IX) by Tandem Conjugate Addition to a Chiral Butenolide.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Asymmetric synthesis of dibenzylbutyrolactones and aryltetralin lignan lactones by tandem conjugate addition to a chiral butenolide

Addition of sulfur-stabilised carbanions to (–)-5-(1-menthyloxy)furan-2(5H)-one followed by reaction with an aromatic aldehyde affords a short synthesis of enantiomerically pure dibenzylbutyrolactone derivatives. Desulfurisation with NaBH4/NiCl2 proceeds in almost quantitative yield, and reduction with NaBH4/KOH gives the parent dibenzylbutyroactones including (–)-6-epi-podorhizol. These undergo cyclisation with acid to give homochiral aryltetralins including (–)-deoxyisopodophyllotoxin in high yield.

Stereoselective synthesis of β-oxy- and α-methylene-γ-butyrolactones on pyranose templates

Reaction of sugar derived epoxy triflates 1 and 2 or epoxy ketoses 11 and 12 with ester or acid enolates followed by acid-catalyzed ring closure affords poly-substituted chiral butenolides in excellent yields.

Efficient and diastereoselective synthesis of (+)‐ and (−)‐grandisol and 2‐[(1R,2S)‐2‐isopropenylcyclobutyl]ethanol (demethylgrandisol) in high purity

AbstractAcetone‐sensitized [2 + 2] photocycloaddition of ethylene to chiral butenolides 3 and 15 yields diastereomeric cyclobutanes, which are transformed to (+)‐(1) and (−)‐grandisol (ent‐1) (overall yield 34–36%) and to 2‐[(1R,2S)‐2‐isopropenylcyclobutyl]ethanol (demethylgrandisol) (2) (overall yield 25%) in five steps.

An approach to the stereocontrolled synthesis of polysubstituted chiral butenolides and γ-lactones

The enantioselective synthesis of polysubstituted butenolides and γ-lactones by an intramolecular Michael addition of chiral thiophenylacetates of γ-hydroxy-α,β-unsaturated esters is described.

ChemInform Abstract: Asymmetric Synthesis of Homochiral Dibenzylbutyrolactone Lignans by Conjugate Addition to a Chiral Butenolide.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

An enantioselective total synthesis of epiisopodophyllotoxin

An enantioselective total synthesis of epiisopodophyllotoxin in which an asymmetric Diels- Alder reaction between a chiral butenolide and an alpha oxy ortho xylylene as the key step is described.

Asymmetric synthesis of homochiral dibenzylbutyrolactone lignans by conjugate addition to a chiral butenolide

Addition of sulphur stabilised carbanions to a chiral non-racemic butenolide followed by reaction with an aromatic aldehyde affords a short synthesis of homochiral dibenzylbutyrolactone derivatives. Desulphurisation of the first formed adducts proceeds in almost quantitative yield to afford the parent lignan.

ChemInform Abstract: Diels‐Alder Cycloadditions of Chiral Butenolides with Cyclopentadiene: endo/exo Selectivity.

Abstract Chiral butenolides are revealed to be good dienophiles in Diels-Alder reactions with cyclopentadiene, affording endo and exo adducts, whose fully characterization is provided. Selectivity of these cycloaddition reactions has been shown to be temperature dependent not as a result of a thermodynamic equilibrium between the isomers, but due to a kinetically controlled process.

Diels-alder cycloadditions of chiral butenolides with cyclopentadiene: endo/exo selectivity

Chiral butenolides are revealed to be good dienophiles in Diels-Alder reactions with cyclopentadiene, affording endo and exo adducts, whose fully characterization is provided. Selectivity of these cycloaddition reactions has been shown to be temperature dependent not as a result of a thermodynamic equilibrium between the isomers, but due to a kinetically controlled process.

Stereoselective reactions. XVI. Total synthesis of (-)-.BETA.-bourbonene by employing asymmetric (2+2) photocycloaddition reaction of chiral butenolide.

Total synthesis of (-)-β-bourbonene (3) was achieved by employing the (2+2) photocycloaddition reaction of (S)-γ-pivaloyloxymethyl-β-methyl-γ-butenolide (5e) with cyclopentenone ethyleneacetal (15). The major photoadduct (16) was readily converted to the cis, anti, cis-tricyclo[5.3.0.02, 6]decane system (22) in 70% yield. Further transformation provided the optically pure title compound (3).

ChemInform Abstract: Diels‐Alder Cycloadditions of Chiral Butenolides with Butadiene and Isoprene: Diastereofacial Selectivity and Regioselectivity.

ChemInformVolume 19, Issue 30 Heterocyclic Compounds ChemInform Abstract: Diels-Alder Cycloadditions of Chiral Butenolides with Butadiene and Isoprene: Diastereofacial Selectivity and Regioselectivity. R. M. ORTUNO, R. M. ORTUNO Dep. Quim., Univ. Auton. Barcelona, E-08193 Bellaterra, Barcelona, SpainSearch for more papers by this authorM. BALLESTEROS, M. BALLESTEROS Dep. Quim., Univ. Auton. Barcelona, E-08193 Bellaterra, Barcelona, SpainSearch for more papers by this authorJ. CORBERA, J. CORBERA Dep. Quim., Univ. Auton. Barcelona, E-08193 Bellaterra, Barcelona, SpainSearch for more papers by this authorF. SANCHEZ-FERRANDO, F. SANCHEZ-FERRANDO Dep. Quim., Univ. Auton. Barcelona, E-08193 Bellaterra, Barcelona, SpainSearch for more papers by this authorJ. FONT, J. FONT Dep. Quim., Univ. Auton. Barcelona, E-08193 Bellaterra, Barcelona, SpainSearch for more papers by this author R. M. ORTUNO, R. M. ORTUNO Dep. Quim., Univ. Auton. Barcelona, E-08193 Bellaterra, Barcelona, SpainSearch for more papers by this authorM. BALLESTEROS, M. BALLESTEROS Dep. Quim., Univ. Auton. Barcelona, E-08193 Bellaterra, Barcelona, SpainSearch for more papers by this authorJ. CORBERA, J. CORBERA Dep. Quim., Univ. Auton. Barcelona, E-08193 Bellaterra, Barcelona, SpainSearch for more papers by this authorF. SANCHEZ-FERRANDO, F. SANCHEZ-FERRANDO Dep. Quim., Univ. Auton. Barcelona, E-08193 Bellaterra, Barcelona, SpainSearch for more papers by this authorJ. FONT, J. FONT Dep. Quim., Univ. Auton. Barcelona, E-08193 Bellaterra, Barcelona, SpainSearch for more papers by this author First published: July 26, 1988 https://doi.org/10.1002/chin.198830183Read 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 onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume19, Issue30July 26, 1988 RelatedInformation

Vitamin C and isovitamin C derived chemistry. 3. Chiral butenolides via efficient 2,3-didehydroxylations of L-gulono-, D-mannono-, and D-ribono-1,4-lactones

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTVitamin C and isovitamin C derived chemistry. 3. Chiral butenolides via efficient 2,3-didehydroxylations of L-gulono-, D-mannono-, and D-ribono-1,4-lactonesJozef A. J. M. Vekemans, Gabriel A. M. Franken, Cornelis W. M. Dapperens, Erik F. Godefroi, and Gordon J. F. ChittendenCite this: J. Org. Chem. 1988, 53, 3, 627–633Publication Date (Print):February 1, 1988Publication History Published online1 May 2002Published inissue 1 February 1988https://doi.org/10.1021/jo00238a028RIGHTS & PERMISSIONSArticle Views696Altmetric-Citations41LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (971 KB) Get e-Alerts Get e-Alerts

Asymmetric 1,3-dipolar cycloadditions to 5-menthyloxy-2[5H]-furanones.

Cycloadditions of various 1,3-dipolar reagents to chiral butenolides 1 and 5 proceed with diastereomeric excess of 20–100%.

High pressure induced Diels-Alder cycloadditions of butenolides to electron-rich dienes

β-Angelica lactone, a model of chiral butenolides, has been efficiently reacted with electron-rich dienes under high pressure conditions, with an excellent diastereofacial, regio- and endo-selectivity, giving the expected adducts in good yields. Some derivatives have been prepared.

Diels-alder cycloadditions of chiral butenolides with butadiene and isoprene:diastereofacial selectivity and regioselectivity

Chiral butenolides react with butadiene at 210° giving optically active bicyclic compounds with excellent diastereoselectivity, in good yields. Optical purity of the adducts has been verified either by chemical correlation and/or by the use of Eu(hfc) 3. Reactions with isoprene at 125–220° afford 1:1 mixtures of regioisomers, selectivity being increased by the use of AlCl 3 as catalyst, at lower temperatures.

ChemInform Abstract: Chiral Butenolides in Diels‐Alder Cycloadditions with Isoprene and Cyclopentadiene.

AbstractCycloaddition of the chiral butenolides (I) with cyclopentadiene (II) yields the endo‐ (III) and exo‐adducts (IV).

ChemInform Abstract: Chiral Oxabicyclic Systems from Ribonolactone.

AbstractA novel and efficient synthesis of the chiral butenolide (IV) is described starting from the ribonolactone (I) which allows the preparation of (IV) on a multi‐gram scale.

Chiral butenolides in diels-alder cycloadditions with isoprene and cyclopentadiene

Chiral α,β-butenolides react with isoprene at 125–220° giving a 1:1 mixture of Diels-Alder regioisomers, selectivity being dramatically increased by the use of AlCl 3 as catalyst. While these butenolides give no reaction with furan even in the presence of catalysts, they react smoothly with cyclopentadiene, endo / exo selectivity being temperature dependent.

ChemInform Abstract: Chiral Butenolides as Dienophiles in Diels‐Alder Cycloadditions.

Chemischer InformationsdienstVolume 17, Issue 25 Preparative Organic Chemistry ChemInform Abstract: Chiral Butenolides as Dienophiles in Diels-Alder Cycloadditions. R. M. ORTUNO, R. M. ORTUNOSearch for more papers by this authorJ. CORBERA, J. CORBERASearch for more papers by this authorJ. FONT, J. FONTSearch for more papers by this author R. M. ORTUNO, R. M. ORTUNOSearch for more papers by this authorJ. CORBERA, J. CORBERASearch for more papers by this authorJ. FONT, J. FONTSearch for more papers by this author First published: June 24, 1986 https://doi.org/10.1002/chin.198625123Read 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 onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume17, Issue25June 24, 1986 RelatedInformation