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  1. Article ; Online: Gold(I)-catalyzed cascade cyclization of allenyl epoxides.

    Tarselli, Michael A / Zuccarello, J Lucas / Lee, Stephen J / Gagné, Michel R

    Organic letters

    2009  Volume 11, Issue 15, Page(s) 3490–3492

    Abstract: Cationic gold(I) phosphite catalysts activate allenes for epoxide cascade reactions. The system is tolerant of numerous functional groups (sulfones, esters, ethers, sulfonamides) and proceeds at room temperature in dichloromethane. The cyclization ... ...

    Abstract Cationic gold(I) phosphite catalysts activate allenes for epoxide cascade reactions. The system is tolerant of numerous functional groups (sulfones, esters, ethers, sulfonamides) and proceeds at room temperature in dichloromethane. The cyclization pathway is sensitive to the substitution pattern of the epoxide and the backbone structure of the A-ring. It is capable of producing medium-ring ethers, fused 6-5 bicyclic, and linked pyran-furan structures. The resulting cycloisomers are reminiscent of structures found in numerous polyether natural products.
    MeSH term(s) Alkadienes/chemistry ; Catalysis ; Crystallography, X-Ray ; Cyclization ; Epoxy Compounds/chemistry ; Gold/chemistry ; Methylene Chloride/chemistry ; Pyrans/chemistry
    Chemical Substances Alkadienes ; Epoxy Compounds ; Pyrans ; propadiene (4AV0LZ8QKB) ; Methylene Chloride (588X2YUY0A) ; Gold (7440-57-5)
    Language English
    Publishing date 2009-07-08
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/ol901391s
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A.

    Crimmins, Michael T / Zuccarello, J Lucas / Cleary, Pamela A / Parrish, Jonathan D

    Organic letters

    2006  Volume 8, Issue 1, Page(s) 159–162

    Abstract: reaction: see text] A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi-Sakurai reactions were central operations in the ... ...

    Abstract [reaction: see text] A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi-Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner-Wadsworth-Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A.
    MeSH term(s) Marine Toxins/chemical synthesis ; Marine Toxins/chemistry ; Molecular Structure ; Oxocins/chemical synthesis ; Oxocins/chemistry ; Stereoisomerism
    Chemical Substances Marine Toxins ; Oxocins ; Brevetoxin A (98112-41-5)
    Language English
    Publishing date 2006-01-05
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7060
    ISSN 1523-7060
    DOI 10.1021/ol0526625
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Enantioselective total synthesis of brevetoxin A: convergent coupling strategy and completion.

    Crimmins, Michael T / Zuccarello, J Lucas / McDougall, Patrick J / Ellis, J Michael

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2009  Volume 15, Issue 36, Page(s) 9235–9244

    Abstract: A highly convergent, enantioselective total synthesis of brevetoxin A is reported. The development of a [X+2+X] Horner-Wadsworth-Emmons/cyclodehydration/reductive etherification convergent coupling strategy allowed a unified approach to the synthesis of ... ...

    Abstract A highly convergent, enantioselective total synthesis of brevetoxin A is reported. The development of a [X+2+X] Horner-Wadsworth-Emmons/cyclodehydration/reductive etherification convergent coupling strategy allowed a unified approach to the synthesis of two advanced tetracyclic fragments from four cyclic ether subunits. The Horner-Wittig coupling of the two tetracyclic fragments provided substrates that were explored for reductive etherification, the success of which delivered a late-stage tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.
    MeSH term(s) Catalysis ; Cyclization ; Ethers, Cyclic/chemical synthesis ; Ethers, Cyclic/chemistry ; Marine Toxins/chemical synthesis ; Marine Toxins/chemistry ; Molecular Structure ; Oxocins/chemical synthesis ; Oxocins/chemistry ; Stereoisomerism
    Chemical Substances Ethers, Cyclic ; Marine Toxins ; Oxocins ; Brevetoxin A (98112-41-5)
    Language English
    Publishing date 2009-08-06
    Publishing country Germany
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.200900777
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Enantioselective total synthesis of brevetoxin A: unified strategy for the B, E, G, and J subunits.

    Crimmins, Michael T / Ellis, J Michael / Emmitte, Kyle A / Haile, Pamela A / McDougall, Patrick J / Parrish, Jonathan D / Zuccarello, J Lucas

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2009  Volume 15, Issue 36, Page(s) 9223–9234

    Abstract: Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy ... ...

    Abstract Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium-ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.
    MeSH term(s) Alkylation ; Cyclization ; Ethers/chemical synthesis ; Ethers/chemistry ; Marine Toxins/chemical synthesis ; Marine Toxins/chemistry ; Molecular Structure ; Oxocins/chemical synthesis ; Oxocins/chemistry ; Stereoisomerism ; Structure-Activity Relationship
    Chemical Substances Ethers ; Marine Toxins ; Oxocins ; Brevetoxin A (98112-41-5)
    Language English
    Publishing date 2009-08-04
    Publishing country Germany
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.200900776
    Database MEDical Literature Analysis and Retrieval System OnLINE

    Full text online

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  5. Article ; Online: Total synthesis of brevetoxin A.

    Crimmins, Michael T / Zuccarello, J Lucas / Ellis, J Michael / McDougall, Patrick J / Haile, Pamela A / Parrish, Jonathan D / Emmitte, Kyle A

    Organic letters

    2008  Volume 11, Issue 2, Page(s) 489–492

    Abstract: A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that ... ...

    Abstract A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.
    MeSH term(s) Aldehydes/chemistry ; Alkenes/chemistry ; Marine Toxins/chemical synthesis ; Marine Toxins/chemistry ; Oxidation-Reduction ; Oxocins/chemical synthesis ; Oxocins/chemistry ; Substrate Specificity
    Chemical Substances Aldehydes ; Alkenes ; Marine Toxins ; Oxocins ; Brevetoxin A (98112-41-5)
    Language English
    Publishing date 2008-12-20
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/ol802710u
    Database MEDical Literature Analysis and Retrieval System OnLINE

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