Corey Lactone Research Articles

Efficient enzymatic preparation of (+)- and (-)-corey lactone derivatives.

Two pairs of Corey lactone derivatives, (+)-1, (-)-2 and (+)-3, (-)-4 have been efficiently prepared in high optical purity by enzymatic esterification and enzymatic hydrolysis catalyzed by lipases from Pseudomonas sp.

Synthesis of corey lactone via highly stereoselective asymmetric diels-alder reaction

We have succeeded in a highly stereoselective asymmetric Diels-Alder reaction between a chiral acrylate 3a derived from commercially available D-pantolactone 2 and 5-benzyloxymethyl-cyclopentadiene 4 to give the adduct 5a in 94% d.e. and 79% yield for the synthesis of Corey lactone 1 .

Prostanoids and Related Compounds. IV. Toral Synthesis of Clavulones.

An efficient and stereoselective synthesis of optically active clavulones has been accomplished by the use of the unnatural type dichloro Corey lactone 1 as a chiral pool.

Synthesis of 1,3-dioxin-4-ones and their use in synthesis. XX. (6S, 7S, 10R)- and (6R, 7S, 10R)-7-isopropyl-10-metyyl-4-oxo-1,5-dioxaspiro(5.5)undec-2-enes; Synthesis and their use in enantiomerically pure corey lactone analogue synthesis.

Two chiral spirocyclic dioxinones (S-5 and R-5) useful in teh so-called de Mayo reaction as alternatives to β-diketones (enones) have been synthesized; they not only act as formylacetates (inactive by themselves as enones) but also display remarkable diastereofacial selectivities in photoaddition to alkenes. The sythesis of these dioxinones is described, together with a practicl one-pot synthesis of enantiomerically pure (1S, 4R)-(+)-6-formyl-2-oxabicyclo[3.3.0]oct-6-en-3-one, the key intermediated of prostaglandin synthesis, from the (6S)-spirocyclic dioxinone (S-5).

Chemoenzymatic large-scale preparation of homochiral bicyclo[3.2.0]hept-2-en-6-one

Both enantiomers of bicyclo[3.2.0]hept-2-en-6-one —precursors of Corey's lactone — were obtained in >98% e.e. by means of an enzymatic resolution of (±)-endo-bicyclo[3.2.0]hept-2-en-6-yl acetate usingPseudomonas fluorescens lipase.

ChemInform Abstract: From Carbohydrates to Carbocycles. Part 2. A Free Radical Route to Corey Lactone and Other Prostanoid Intermediates.

ChemInformVolume 20, Issue 12 Heterocyclic Compounds ChemInform Abstract: From Carbohydrates to Carbocycles. Part 2. A Free Radical Route to Corey Lactone and Other Prostanoid Intermediates. T. V. RAJANBABU, T. V. RAJANBABU E. I. DuPont de Nemours&Co., Central Res. &Dev. Dep., Exper. Station, Wilmington, DE 19898, USASearch for more papers by this author T. V. RAJANBABU, T. V. RAJANBABU E. I. DuPont de Nemours&Co., Central Res. &Dev. Dep., Exper. Station, Wilmington, DE 19898, USASearch for more papers by this author First published: March 21, 1989 https://doi.org/10.1002/chin.198912170AboutPDF 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 onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume20, Issue12March 21, 1989 RelatedInformation

Total Synthesis of 15-Oxo-13,14-Dihydro-prostaglandin F2α, A Major Metabolite of Prostaglandin F2α

Abstract The synthesis of prostaglandin F2α metabolite starting from the Corey lactone is described. The key step of the synthesis involves chemoselective Wittig reaction.

Large-scale synthesis of racemic “Corey lactone”

Very convenient synthesis of Corey lactone–(3aα,4α,5β,6aα)-5-(1,1'-biphenyl-4-carbonyloxy)-hexahydro-4-hydroxymethyl-2H-cyclopenta[b]furan-2-one (VI) was developed. The title compound was obtained in five steps starting from 7-anti-hydroxymethyl-5-exo-chloro-bicyclo[2.2.1]-heptan-2-one (I) in a very good overall yield.

ChemInform Abstract: Conversion of Aucubin to a Useful Corey Lactone Analogue for the Synthesis of 11‐Methyl PGA2.

ChemInform Abstract: Conversion of Aucubin to a Useful Corey Lactone Analogue for the Synthesis of 11‐Methyl PGA2.

From carbohydrates to carbocycles. 2. A free radical route to Corey lactone and other prostanoid intermediates

From carbohydrates to carbocycles. 2. A free radical route to Corey lactone and other prostanoid intermediates

Conversion of aucubin to a useful Corey lactone analog for the synthesis of 11-methyl PGA2

Conversion de l'aucubine en dimethylacetal de methyl-5 oxo-2 tetrahydro-3,3a,4,6a cyclopenta [b] furannecarbaldehyde-4

Synthesis of the major urinary metabolite of prostaglandin D2

Starting from the Corey lactone (3), the total synthesis of a specific urinary metabolite of prostaglandin D2, viz., (Z)-9α,11β-dihydroxy-15-oxo-2,3,18,19-tetranorprost-5-ene-1,20-dioic acid (1) and its 5E-isomer is described. The synthetic material was isolated in a tricyclic form as the corresponding hemiacetal lactone (2). The g.c.m.s. characteristics of the methyl ester, trimethylsilyl ether derivative of this compound were identical with those previously described for the same derivative of the 11β-tetranor metabolite of PGD2.

1,3-ジオキシン-4-オン類の合成と有機合成への応用 : 最近の進歩

Several synthetic methods of 1, 3-dioxin-4-one and its derivatives are described. These dioxinones undergo cycloreversion to formyl- or acylketenes, whose inter- or intramolecular trapping provides efficient routes to a variety of heterocyclic compounds. Use of 6-unsubstituted dioxinones in the so-called de Mayo reaction provides an efficient method for simultaneous introduction of acetic acid and formyl appendages at the vicinal position of alkanes. Chiral spirocyclic dioxinones readily available from l-menthone show remarkable diastereofacial selectivities in a variety of addition reactions, such as photo [2+2] additions, Diels-Alder reactions, and conjugated additions. Thus, use of spirocyclic dioxinones has provided enantioselective synthetic methods of Corey lactone derivatives, carbocyclic analogues of C-nucleoside, and 3-hydroxybutyric acid.

ChemInform Abstract: Synthesis of Biologically Active Compounds Using Photochemical Pericyclic Reactions

Novel Synthetic approaches to β-lactams and Corey lactone analogues via four-membered ring intermediates formed by photochemical pericyclic reaction, followed by subsequent retro-aldol-type C-C bond fission are described. The same approach to carbocyclic C-nucleosides which involves thermal 4 + 2 addition reaction in the first step is also reported. These examples demonstrate that pericyclic reactions, if combined with C-C bond fission of the carbocyclic rings thus formed, provide productive synthetic methods of biologically active substances which allow strict regio-and stereochemical control of the required functionality of the target molecules.

ChemInform Abstract: Synthesis of a Corey Lactone Analogue from Iridoid Glucoside Aucubin and Its Utilization in the Synthesis of a New 12‐epi‐PGF2α Modified at C‐11.

AbstractHexaacetylaucubin (I) is oxidized to form the lactone (II) which yields the acid (IIIb) upon methanolysis and subsequent saponification.

Synthesis of a Corey lactone analog from the iridoid glucoside aucubin and its utilization in the synthesis of a new 12-epi-PGF2.alpha. modified at C-11

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of a Corey lactone analog from the iridoid glucoside aucubin and its utilization in the synthesis of a new 12-epi-PGF2.alpha. modified at C-11Romolo Bernini, Enrico Davini, Carlo Iavarone, and Corrado TrogoloCite this: J. Org. Chem. 1986, 51, 24, 4600–4603Publication Date (Print):November 1, 1986Publication History Published online1 May 2002Published inissue 1 November 1986https://doi.org/10.1021/jo00374a021RIGHTS & PERMISSIONSArticle Views350Altmetric-Citations19LEARN 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 (603 KB) Get e-Alerts Get e-Alerts

ChemInform Abstract: A Novel Approach to Prostaglandins from the Corey Lactone Involving BF3‐Mediated Reactions of a Sulphone and Aldehydes.

AbstractDas Lacton (I) liefert in literaturbekannten Reaktionsschritten über (IIa)‐(IIe) das Sulfon (III), das mit den Aldehyden (IV) über die Anionen von (III) zu (V) substituiert wird.

光化学的周辺環状反応を用いる生理活性化合物の合成

Novel Synthetic approaches to β-lactams and Corey lactone analogues via four-membered ring intermediates formed by photochemical pericyclic reaction, followed by subsequent retro-aldol-type C-C bond fission are described. The same approach to carbocyclic C-nucleosides which involves thermal 4 + 2 addition reaction in the first step is also reported. These examples demonstrate that pericyclic reactions, if combined with C-C bond fission of the carbocyclic rings thus formed, provide productive synthetic methods of biologically active substances which allow strict regio-and stereochemical control of the required functionality of the target molecules.

One-pot conversion of 6-hydroxy-.DELTA.7-iridoid glucosides into cis-2-oxabicyclo[3.3.0]oct-7-enes and transformation into Corey's lactone analog

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOne-pot conversion of 6-hydroxy-.DELTA.7-iridoid glucosides into cis-2-oxabicyclo[3.3.0]oct-7-enes and transformation into Corey's lactone analogCarlo Bonini, Carlo Iavarone, Corrado Trogolo, and Romano Di FabioCite this: J. Org. Chem. 1985, 50, 7, 958–961Publication Date (Print):April 1, 1985Publication History Published online1 May 2002Published inissue 1 April 1985https://doi.org/10.1021/jo00207a010RIGHTS & PERMISSIONSArticle Views298Altmetric-Citations17LEARN 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 (487 KB) Get e-Alerts Get e-Alerts

Synthesis of clavulones (claviridenones)

New marine eicosanoid clavulones (claviridenones) were synthesized from the Corey lactone and D-glutamic acid.