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  1. Article ; Online: Total Synthesis of Marine Polyketide Plakortone Q.

    Okazaki, Shinnosuke / Senda, Kaho / Tokuta, Ayaka / Inagaki, Misa / Kamaike, Kazuo / Ota, Koichiro / Miyaoka, Hiroaki

    Chemical & pharmaceutical bulletin

    2024  Volume 72, Issue 2, Page(s) 179–185

    Abstract: The total synthesis of the natural bicyclo[3.3.0]furanolactone polyketide, plakortone Q, was achieved in 24 steps from (R)-Roche ester. The main feature of this synthetic strategy is the stereoselective construction of a central tetrahydrofuran moiety ... ...

    Abstract The total synthesis of the natural bicyclo[3.3.0]furanolactone polyketide, plakortone Q, was achieved in 24 steps from (R)-Roche ester. The main feature of this synthetic strategy is the stereoselective construction of a central tetrahydrofuran moiety with four consecutive stereoisomeric centers using the Upjohn dihydroxylation of oxiranyl-substituted alkenes and acid-mediated 5-endo-tet cyclization.
    MeSH term(s) Polyketides ; Cyclization ; Stereoisomerism ; Alkenes
    Chemical Substances Polyketides ; Alkenes
    Language English
    Publishing date 2024-02-03
    Publishing country Japan
    Document type Journal Article
    ZDB-ID 213307-6
    ISSN 1347-5223 ; 0009-2363
    ISSN (online) 1347-5223
    ISSN 0009-2363
    DOI 10.1248/cpb.c23-00876
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 770: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (1.OG)
    ab Jg. 2022: Lesesaal (EG)

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  2. Article: Total Synthesis and Structure Revision of Saniculamoid D

    Ota, Koichiro / Kamaike, Kazuo / Miyaoka, Hiroaki

    Synlett

    2023  Volume 34, Issue 19, Page(s) 2304–2308

    Abstract: We present the first asymmetric total synthesis of the norsesquiterpenoid saniculamoid D, from a previously known pure chiral imide, with a longest linear sequence of seven steps. The key highlight of the synthesis is the formation of the bicyclo[3.1.0] ... ...

    Abstract We present the first asymmetric total synthesis of the norsesquiterpenoid saniculamoid D, from a previously known pure chiral imide, with a longest linear sequence of seven steps. The key highlight of the synthesis is the formation of the bicyclo[3.1.0]hexane moiety through the Julia–Kocienski olefination and Hodgson cyclopropanation. Notably, the NMR spectra and specific rotation value of the synthesized structure did not agree with those of the natural compound. However, a meticulous comparison of the data prompted the reassignment of the correct structure of saniculamoid D, which now corresponds to the structure initially proposed for chromolaevanedione.
    Keywords saniculamoid D ; chromolaevanedione ; norsesquiterpenoid ; bicyclo[3.1.0]hexane ; total synthesis ; structure revision
    Language English
    Publishing date 2023-08-03
    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-2147-9454
    Database Thieme publisher's database

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  3. Article ; Online: Total Synthesis of Chlorinated Oxylipin Eiseniachloride B.

    Ota, Koichiro / Kamaike, Kazuo / Miyaoka, Hiroaki

    Chemical & pharmaceutical bulletin

    2021  Volume 69, Issue 6, Page(s) 590–594

    Abstract: Eiseniachloride B is a marine chlorinated oxylipin isolated from the brown alga Eisenia bicyclis. This natural product contains cyclopentane, chlorohydrin, and 14-membered lactone systems that incorporate five stereogenic centers. In this paper, we ... ...

    Abstract Eiseniachloride B is a marine chlorinated oxylipin isolated from the brown alga Eisenia bicyclis. This natural product contains cyclopentane, chlorohydrin, and 14-membered lactone systems that incorporate five stereogenic centers. In this paper, we report on the total synthesis of structurally unique oxylipin eiseniachloride B from optically active lactol via ecklonialactone B in a linear sequence comprising 11 steps with a 12.1% overall yield.
    MeSH term(s) Biological Products/chemical synthesis ; Biological Products/chemistry ; Halogenation ; Lactones/chemical synthesis ; Lactones/chemistry ; Molecular Conformation ; Oxylipins/chemical synthesis ; Oxylipins/chemistry ; Phaeophyceae/chemistry ; Stereoisomerism
    Chemical Substances Biological Products ; Lactones ; Oxylipins ; ecklonialactone B (121923-96-4)
    Language English
    Publishing date 2021-05-19
    Publishing country Japan
    Document type Journal Article
    ZDB-ID 213307-6
    ISSN 1347-5223 ; 0009-2363
    ISSN (online) 1347-5223
    ISSN 0009-2363
    DOI 10.1248/cpb.c21-00091
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 770: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (1.OG)
    ab Jg. 2022: Lesesaal (EG)

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  4. Article: Total syntheses of ent-hypocoprin A and ent-hypocoprin B

    Ota, Koichiro / Watanabe, Taiki / Igarashi, Shuntaro / Okazaki, Shinnosuke / Kamaike, Kazuo / Miyaoka, Hiroaki

    RSC advances. 2022 June 06, v. 12, no. 26

    2022  

    Abstract: This study reports the stereoselective total syntheses of the antipodes of the unique 3/10 bicyclic skeletal sesquiterpenoids, namely, hypocoprin A and hypocoprin B. The synthesis involved conjugate addition accelerated by trimethylsilyl chloride, ... ...

    Abstract This study reports the stereoselective total syntheses of the antipodes of the unique 3/10 bicyclic skeletal sesquiterpenoids, namely, hypocoprin A and hypocoprin B. The synthesis involved conjugate addition accelerated by trimethylsilyl chloride, construction of the ten-membered ring via the intramolecular SN2 reaction promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene, and osmium-mediated π-facial selective dihydroxylation to functionalize the 1,1-disubstituted alkene.
    Keywords chlorides ; dihydroxylation ; sesquiterpenoids ; stereoselectivity
    Language English
    Dates of publication 2022-0606
    Size p. 16576-16580.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ISSN 2046-2069
    DOI 10.1039/d2ra02891c
    Database NAL-Catalogue (AGRICOLA)

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  5. Article: Total Synthesis and Structural Revision of Cephalosporolide J

    Ota, Koichiro / Kamaike, Kazuo / Miyaoka, Hiroaki

    Synlett

    2022  Volume 34, Issue 03, Page(s) 271–276

    Abstract: Herein, we report the first total synthesis of cephalosporolide J, which is a deep sea sediment derived polyketide harboring a unique bicyclo[3.3.0]furanolactone moiety. The adopted synthetic strategy consisted of the alkynylation of γ-lactone with ... ...

    Abstract Herein, we report the first total synthesis of cephalosporolide J, which is a deep sea sediment derived polyketide harboring a unique bicyclo[3.3.0]furanolactone moiety. The adopted synthetic strategy consisted of the alkynylation of γ-lactone with lithium alkynyltrifluoroborate followed by a spiroketalization triggered by hydrogenation of the triple bond. Through this synthesis, the correct structure of cephalosporolide J is shown to be that of the 9- epi stereoisomer of the structure originally proposed.
    Keywords cephalosporolide J ; polyketide ; bicyclo[3.3.0]furanolactone ; total synthesis ; structural revision
    Language English
    Publishing date 2022-10-24
    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-1967-1284
    Database Thieme publisher's database

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  6. Article ; Online: Total syntheses of

    Ota, Koichiro / Watanabe, Taiki / Igarashi, Shuntaro / Okazaki, Shinnosuke / Kamaike, Kazuo / Miyaoka, Hiroaki

    RSC advances

    2022  Volume 12, Issue 26, Page(s) 16576–16580

    Abstract: This study reports the stereoselective total syntheses of the antipodes of the unique 3/10 bicyclic skeletal sesquiterpenoids, namely, hypocoprin A and hypocoprin B. The synthesis involved conjugate addition accelerated by trimethylsilyl chloride, ... ...

    Abstract This study reports the stereoselective total syntheses of the antipodes of the unique 3/10 bicyclic skeletal sesquiterpenoids, namely, hypocoprin A and hypocoprin B. The synthesis involved conjugate addition accelerated by trimethylsilyl chloride, construction of the ten-membered ring
    Language English
    Publishing date 2022-06-06
    Publishing country England
    Document type Journal Article
    ISSN 2046-2069
    ISSN (online) 2046-2069
    DOI 10.1039/d2ra02891c
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Biomimetic total synthesis of plakortone Q

    Okazaki, Shinnosuke / Senda, Kaho / Tokuta, Ayaka / Inagaki, Misa / Kamaike, Kazuo / Ota, Koichiro / Miyaoka, Hiroaki

    Organic & biomolecular chemistry

    2022  Volume 20, Issue 34, Page(s) 6771–6775

    Abstract: Plakortone Q and plakdiepoxide are natural polyketides isolated from the marine ... ...

    Abstract Plakortone Q and plakdiepoxide are natural polyketides isolated from the marine sponge
    MeSH term(s) Animals ; Biomimetics ; Cyclization ; Lactones ; Polyketides/pharmacology ; Porifera ; Stereoisomerism
    Chemical Substances Lactones ; Polyketides
    Language English
    Publishing date 2022-08-31
    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/d2ob01032a
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article: Unified Approach to ent-Eudesmane-Type Terpenoid Synthesis: Total Synthesis of Sinupol and Eutyscoparin A

    Ota, Koichiro / Kamaike, Kazuo / Miyaoka, Hiroaki

    Synthesis

    2021  Volume 54, Issue 03, Page(s) 689–696

    Abstract: ent -Eudesmane-type terpenoids constitute a large class of natural products derived from plants, animals, and bacteria. We describe a synthetic approach to two ent -eudesmane-type terpenoids, sinupol and eutyscoparin A, that relies on a key π-facial- ... ...

    Abstract ent -Eudesmane-type terpenoids constitute a large class of natural products derived from plants, animals, and bacteria. We describe a synthetic approach to two ent -eudesmane-type terpenoids, sinupol and eutyscoparin A, that relies on a key π-facial- and endo exo -selective intramolecular Diels–Alder reaction to set the C-5–C-10 stereotriads. Further key transformations of trans -fused decalin include conversion to methyl ketone via a versatile thioester intermediate and appropriate functionalization toward target compounds.
    Keywords -eudesmane ; sinupol ; eutyscoparin A ; total synthesis ; Diels–Alder reaction ; protecting-group-free
    Language English
    Publishing date 2021-09-13
    Publisher Georg Thieme Verlag KG
    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/a-1643-5729
    Database Thieme publisher's database

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  9. Article: Total Synthesis of Ascospiroketal B

    Hara, Yoshiyori / Kamaike, Kazuo / Ota, Koichiro / Miyaoka, Hiroaki

    Synlett

    2020  Volume 31, Issue 17, Page(s) 1730–1734

    Abstract: An enantioselective total synthesis of the marine tricyclic polyketide ascospiroketal B, previously isolated from the marine-derived fungus Ascochyta salicorniae, was accomplished in 21 steps by using an improved route. The intriguing 5,5-spiroketal- ... ...

    Abstract An enantioselective total synthesis of the marine tricyclic polyketide ascospiroketal B, previously isolated from the marine-derived fungus Ascochyta salicorniae, was accomplished in 21 steps by using an improved route. The intriguing 5,5-spiroketal- cis -fused-γ-lactone core was constructed through rearrangement of an epoxide, in conjunction with an acid-mediated spiroketalization.
    Keywords ascospiroketal B ; polyketides ; spiroketals ; rearrangement ; total synthesis
    Language English
    Publishing date 2020-07-30
    Publisher © Georg Thieme Verlag
    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/s-0040-1706405
    Database Thieme publisher's database

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  10. Article: A Versatile, Diels–Alder Reaction-Based Approach to Prenyleudesmane Diterpenoids: A Concise Total Synthesis of Sinupol

    Ota, Koichiro / Kamaike, Kazuo / Miyaoka, Hiroaki

    Synlett

    2020  Volume 31, Issue 10, Page(s) 1007–1010

    Abstract: Herein, a concise strategy designed to provide general and diversifiable access to various prenyleudesmane terpenoids is described and utilized in the asymmetric synthesis of a biologically active prenyleudesmane diterpenoid, sinupol, which is ... ...

    Abstract Herein, a concise strategy designed to provide general and diversifiable access to various prenyleudesmane terpenoids is described and utilized in the asymmetric synthesis of a biologically active prenyleudesmane diterpenoid, sinupol, which is accomplished in a seven-step procedure.
    Keywords prenyleudesmane diterpenoid ; sinupol ; PTP1B inhibitor ; Diels–Alder reaction ; total synthesis
    Language English
    Publishing date 2020-03-20
    Publisher © Georg Thieme Verlag
    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/s-0037-1610757
    Database Thieme publisher's database

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