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  1. Article ; Online: Editorial to the Special Issue "Total Synthesis of Natural Products: A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday".

    Koskinen, Ari M P

    Molecules (Basel, Switzerland)

    2020  Volume 25, Issue 24

    Abstract: Natural products have intrigued humans throughout history [ ... ]. ...

    Abstract Natural products have intrigued humans throughout history [...].
    MeSH term(s) Biological Products/chemical synthesis ; Biological Products/chemistry ; Biological Products/pharmacology ; Chemistry Techniques, Synthetic/history ; Chemistry Techniques, Synthetic/methods ; Famous Persons ; History, 20th Century ; History, 21st Century ; Humans
    Chemical Substances Biological Products
    Language English
    Publishing date 2020-12-10
    Publishing country Switzerland
    Document type Biography ; Editorial ; Historical Article ; Introductory Journal Article
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules25245841
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Editorial to the Special Issue “Total Synthesis of Natural Products

    Ari M. P. Koskinen

    Molecules, Vol 25, Iss 5841, p

    A Themed Issue Dedicated to Professor Dr. Dieter Schinzer for His 65th Birthday”

    2020  Volume 5841

    Abstract: Natural products have intrigued humans throughout history [.] ...

    Abstract Natural products have intrigued humans throughout history [.]
    Keywords n/a ; Organic chemistry ; QD241-441
    Language English
    Publishing date 2020-12-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  3. Article: Diastereoselective Synthesis of Substituted Chromenopyrrolidinones from Amino Acid Derived Nitriles

    Heikinheimo, Annakaisa / Nieger, Martin / Koskinen, Ari M. P.

    Synlett

    2022  Volume 34, Issue 12, Page(s) 1512–1518

    Abstract: Novel substituted chromenopyrrolidinones were synthesized from natural amino acid derivatives through an unprecedented route involving a Knoevenagel/transesterification sequence and an allylative palladium-catalyzed cyclization reaction. The products ... ...

    Abstract Novel substituted chromenopyrrolidinones were synthesized from natural amino acid derivatives through an unprecedented route involving a Knoevenagel/transesterification sequence and an allylative palladium-catalyzed cyclization reaction. The products were nature-inspired heterocycles derived from natural amino acids. The targets were synthesized with varying degrees of stereoselectivity: racemization is a known issue with amino acids, and this provided a formidable challenge to our method development. In total, six derivatives were synthesized in moderate to good yields.
    Keywords pyrrolidinones ; coumarins ; chromenopyrrolidines ; 5- ; - ; cyclization ; amino acid racemization ; asymmetric synthesis
    Language English
    Publishing date 2022-12-04
    Publisher Georg Thieme Verlag KG
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2042012-2
    ISSN 1437-2096 ; 0936-5214
    ISSN (online) 1437-2096
    ISSN 0936-5214
    DOI 10.1055/a-1992-6650
    Database Thieme publisher's database

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  4. Article ; Online: Boron enolate chemistry toward the syntheses of polyketide stereotetrads.

    Koskinen, Ari M P

    Chemical record (New York, N.Y.)

    2014  Volume 14, Issue 1, Page(s) 52–61

    Abstract: In 1976 Mukaiyama published a paper that was to make a major impact on the development of the aldol reaction in the future. Mild enolate formation by treatment of a ketone with dibutylboron triflate in the presence of a tertiary amine generates a ... ...

    Abstract In 1976 Mukaiyama published a paper that was to make a major impact on the development of the aldol reaction in the future. Mild enolate formation by treatment of a ketone with dibutylboron triflate in the presence of a tertiary amine generates a relatively stable boron enolate, which can subsequently react with an aldehyde to give the cross-aldol product in good yields. This reaction has become a reliable tool for the practicing synthetic chemist. Nearly 10000 polyketides are known, and of these about 600 contain the tripropionate unit with a stereotetrad, four contiguous stereocenters with alternating methyl and hydroxyl substituents in the main chain. The versatility of the boron enolate aldol reaction is showcased with selected applications in the synthesis of these structural motifs.
    MeSH term(s) Aldehydes/chemistry ; Boron/chemistry ; Polyketides/chemical synthesis ; Polyketides/chemistry ; Stereoisomerism
    Chemical Substances Aldehydes ; Polyketides ; 3-hydroxybutanal (8C6G962B53) ; Boron (N9E3X5056Q)
    Language English
    Publishing date 2014-02
    Publishing country United States
    Document type Journal Article
    ZDB-ID 2044646-9
    ISSN 1528-0691 ; 1527-8999
    ISSN (online) 1528-0691
    ISSN 1527-8999
    DOI 10.1002/tcr.201300033
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  5. Article: Synthesis of the C1–C12 Fragment of Calyculin C

    Konstantinova, Olga V. / Koskinen, Ari M.P.

    Synthesis

    2018  Volume 51, Issue 01, Page(s) 285–295

    Abstract: Calyculins are a class of highly cytotoxic metabolites originally isolated from the marine sponge Discodermia calyx. To date, a total of twelve different calyculins (A–J) and calyculinamides (A, B and F) have been described, the most abundant (in D. ... ...

    Abstract Calyculins are a class of highly cytotoxic metabolites originally isolated from the marine sponge Discodermia calyx. To date, a total of twelve different calyculins (A–J) and calyculinamides (A, B and F) have been described, the most abundant (in D. calyx ) being calyculins A and C. Herein, we demonstrate a concise route to access the C1–C12 tetraene fragment of calyculin C using transition-metal-catalyzed coupling reactions (Suzuki–Miyaura, Stille, Negishi and Heck) for the key connections. The synthesis starts from propionaldehyde and proceeds in 10 steps with 7.5% overall yield. We also describe an efficient route for the preparation of ( Z )-3-iodobut-2-enenitrile in four steps and 68% yield.
    Keywords calyculins ; natural products ; transition-metal-catalyzed cross-coupling ; Suzuki–Miyaura ; Stille ; Negishi and Heck coupling ; syntheses of di- and polyenes
    Language English
    Publishing date 2018-11-22
    Publisher Georg Thieme Verlag
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/s-0037-1610387
    Database Thieme publisher's database

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  6. Article: Versatile Synthesis of Symmetrical Carbazole-Based Ligand Precursors­ via Regioselective Aromatic Bromination

    Rembiak, Andreas / Koskinen, Ari M. P.

    Synthesis

    2015  Volume 47, Issue 21, Page(s) 3347–3353

    Abstract: A highly efficient synthetic route towards dibrominated, substituted carbazoles via an environmentally benign, regioselective bromination as the key step has been developed. Electron-rich and electron-deficient aromatic as well as aliphatic groups are ... ...

    Abstract A highly efficient synthetic route towards dibrominated, substituted carbazoles via an environmentally benign, regioselective bromination as the key step has been developed. Electron-rich and electron-deficient aromatic as well as aliphatic groups are well tolerated enabling access to these versatile ligand precursors in high overall yields. On larger scale the whole sequence can be performed under chromatography-free conditions.
    Keywords carbazoles ; heterocycles ; tridentate ligands ; regioselective bromination ; chiral oxazolines
    Language English
    Publishing date 2015-08-13
    Publisher © Georg Thieme Verlag
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/s-0034-1378825
    Database Thieme publisher's database

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  7. Article ; Online: Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via η3-allylpalladium intermediates.

    Passiniemi, Mikko / Koskinen, Ari M P

    Organic & biomolecular chemistry

    2011  Volume 9, Issue 6, Page(s) 1774–1783

    Abstract: A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner's aldehyde. The furan framework ... ...

    Abstract A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner's aldehyde. The furan framework is formed via an η(3)-allylpalladium intermediate.
    MeSH term(s) Allyl Compounds/chemistry ; Molecular Structure ; Palladium/chemistry ; Sphingosine/analogs & derivatives ; Sphingosine/chemical synthesis ; Stereoisomerism
    Chemical Substances Allyl Compounds ; pachastrissamine ; Palladium (5TWQ1V240M) ; Sphingosine (NGZ37HRE42)
    Language English
    Publishing date 2011-03-21
    Publishing country England
    Document type Journal Article
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/c0ob00643b
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article: Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxypiperidines - development of a phosphite-driven cyclodehydration.

    Huy, Peter H / Westphal, Julia C / Koskinen, Ari M P

    Beilstein journal of organic chemistry

    2014  Volume 10, Page(s) 369–383

    Abstract: ... triethylphosphite as a substitute for triphenylphosphine is developed. Here the stoichiometric oxidized P(V)-byproduct ...

    Abstract A concise (5 to 6 steps), stereodivergent, highly diastereoselective (dr up to >19:1 for both stereoisomers) and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, a core motif in numerous bioactive compounds, is presented. This sequence allowed an efficient synthesis of the NK-1 inhibitor L-733,060 in 8 steps. Additionally, a cyclodehydration-realizing simple triethylphosphite as a substitute for triphenylphosphine is developed. Here the stoichiometric oxidized P(V)-byproduct (triethylphosphate) is easily removed during the work up through saponification overcoming separation difficulties usually associated to triphenylphosphine oxide.
    Language English
    Publishing date 2014-02-11
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2192461-2
    ISSN 1860-5397
    ISSN 1860-5397
    DOI 10.3762/bjoc.10.35
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  9. Book: Asymmetric synthesis of natural products

    Koskinen, Ari M. P

    2012  

    Abstract: Based on a successful course taught for the last 20 years at universities in the UK, Finland and elsewhere"-- ... Natural product synthesis has played a key role in the development of many synthetic methods and will continue to do so in the future. Many ... ...

    Author's details Ari M. P. Koskinen
    Abstract "Based on a successful course taught for the last 20 years at universities in the UK, Finland and elsewhere"--

    "Natural product synthesis has played a key role in the development of many synthetic methods and will continue to do so in the future. Many recent advances in such diverse fields as immunology, cellular biology and materials science have been achieved through the synthetic chemist's ability to construct often very complicated structures in one enantiomeric form.Asymmetric Synthesis of Natural Products, 2nd Edition introduces students to this rapidly growing field of organic chemistry. The initial chapters present the foundations of asymmetric synthesis, including the theory and applications of individual asymmetric reactions. This is followed by chapters on each of the major individual classes of natural products; their structures, biosynthesis and interrelationships as well as examples of asymmetric syntheses and the practical value of these compounds. Natural product classes covered include carbohydrates, amino acids, peptides, proteins, nucleosides, nucleotides, nucleic acids, polyketides, isoprenoids, shikamic acid derivatives and alkaloids.For this second edition the text has been thoroughly updated and expanded, and includes new discussions and examples covering atom and redox economies, practical aspects and environmental awareness. Organocatalysis has emerged completely in the last ten years, and has been fully integrated into this new edition.Asymmetric Synthesis of Natural Products, 2nd Edition will find a place on the bookshelves of advanced undergraduates and postgraduates working in natural products chemistry, organic synthesis, medicinal chemistry and drug discovery. It is also useful for practising researchers who want to refresh their knowledge of the field"--
    Keywords Asymmetry (Chemistry) ; Natural products/Synthesis
    Language English
    Size XVI, 306 S., graph. Darst.
    Edition 2. ed.
    Publisher Wiley
    Publishing place Hoboken, NJ
    Document type Book
    Note Literaturangaben und Index
    ISBN 1118347331 ; 1119976693 ; 9781118347331 ; 9781119976684 ; 9781119976691 ; 1119976685
    Database Library catalogue of the German National Library of Science and Technology (TIB), Hannover

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  10. Article ; Online: Diastereoselective intramolecular allyl transfer from allyl carbamate accompanied by 5-endo-trig ring closure.

    Karjalainen, Oskari K / Nieger, Martin / Koskinen, Ari M P

    Angewandte Chemie (International ed. in English)

    2013  Volume 52, Issue 9, Page(s) 2551–2554

    Abstract: To All(oc) involved: A palladium-catalyzed formal 5-endo-trig heteroannulation of enones generated in situ from amino acid derived β-keto nitriles has been realized (see scheme; Alloc=allyl carbamate). The reaction proceeds with allyl-group transfer from ...

    Abstract To All(oc) involved: A palladium-catalyzed formal 5-endo-trig heteroannulation of enones generated in situ from amino acid derived β-keto nitriles has been realized (see scheme; Alloc=allyl carbamate). The reaction proceeds with allyl-group transfer from the carbamate protecting group to generate two new contiguous stereocenters, including one quaternary center, with high selectivity.
    Language English
    Publishing date 2013-02-25
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201209443
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