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  • 1
    Language: English
    In: The Journal of organic chemistry, 17 August 2012, Vol.77(16), pp.6929-36
    Description: The total syntheses of both (-)-cryptocaryolone and (-)-cryptocaryolone diacetate is presented herein. The usage of a diastereoselective oxy-Michael addition/benzylidene acetal formation coupled with a selective axial oxocarbenium allylation allowed for the preparation of the α-C-glycoside moiety present in the bicyclic bridged structure. In addition, the syn-1,3-diol of the linear portion was installed via a Wacker oxidation followed by a subsequent directed reduction of the appropriate homoallylic alcohol precursor.
    Keywords: Acetals -- Chemistry ; Alcohols -- Chemistry ; Monosaccharides -- Chemistry ; Pyrones -- Chemical Synthesis
    ISSN: 00223263
    E-ISSN: 1520-6904
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  • 2
    Language: English
    In: The Journal of organic chemistry, 07 October 2011, Vol.76(19), pp.8027-32
    Description: The formal synthesis of the marine natural product (-)-cyanolide A is presented. The synthetic strategy is centered on two acyclic diastereoselective reactions and a single cyclic reaction with modest to excellent dr based on an initial stereocenter. Most notable is a highly stereoselective oxocarbenium reduction based on a "mismatched" reactive conformer to afford the β-C-glycoside subunit leading to an efficient synthesis of the diolide aglycon in 12 overall steps.
    Keywords: Aldehydes -- Chemistry ; Carbon -- Chemistry ; Chemistry Techniques, Synthetic -- Methods ; Macrolides -- Chemical Synthesis
    ISSN: 00223263
    E-ISSN: 1520-6904
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  • 3
    Language: English
    In: Tetrahedron Letters, 2011, Vol.52(40), pp.5124-5127
    Description: The convergent syntheses of two possible diastereomers of the C25–C40 subunit resident in (−)-caylobolide A have been accomplished. The key reaction featured a chemoselective Ru-catalyzed cross-metathesis between a fully elaborated type I and two functionalized type II α,β-unsaturated ketones.
    Keywords: Allylation ; Reduction ; Natural Products ; Cross-Metathesis ; Caylobolide ; Chemistry
    ISSN: 0040-4039
    E-ISSN: 1873-3581
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  • 4
    Language: English
    In: The Journal of organic chemistry, 18 June 2010, Vol.75(12), pp.4095-104
    Description: The formal synthesis of the unnatural (-)-neopeltolide core is discussed in detail. Efficient application of the Evans' protocol for the synthesis of 1,3-syn-diols via an intramolecular hetero-Michael addition followed by reductive deprotection of the resulting benzylidene acetal allowed for swift access to the delta-lactone. Central to the synthetic approach is a tandem nucleophilic addition-diastereoselective axial reduction of an in situ generated oxocarbenium cation to assemble the beta-C-glycoside moiety of the neopeltolide core.
    Keywords: Macrolides -- Chemical Synthesis
    ISSN: 00223263
    E-ISSN: 1520-6904
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  • 5
    Language: English
    In: Tetrahedron Letters, 23 October 2013, Vol.54(43), pp.5826-5829
    Description: The synthesis of a possible 1,5- -polyol C1–C24 subunit resident in (−)-caylobolide A has been accomplished. The key reaction sequence was a repetitive protocol for the construction of the -1,5-diol segment by means of Ru-catalyzed cross-metathesis and boron-mediated allylation reactions.
    Keywords: Allylation ; Conjugate Addition ; Natural Products ; Cross-Metathesis ; Caylobolide ; Chemistry
    ISSN: 0040-4039
    E-ISSN: 1873-3581
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  • 6
    Language: English
    In: Tetrahedron Letters, 14 August 2013, Vol.54(33), pp.4487-4490
    Description: The allylation of various aldehydes with α-substituted allylsilanes in the presence of TiCl has been investigated. It has been shown that these reagents readily allow for good yields and high to excellent diastereoselectivities (up to 〉20:1) for a series of aldehydes, thereby providing a means of preparing non-conjugated ( )-homoallylic alcohols in a single step.
    Keywords: Allylation ; Allylsilane ; Olefination ; Natural Products ; Diastereoselective Synthesis ; Chemistry
    ISSN: 0040-4039
    E-ISSN: 1873-3581
    Source: ScienceDirect Journals (Elsevier)
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  • 7
    Language: English
    In: Tetrahedron Letters, 24 July 2013, Vol.54(30), pp.3990-3992
    Description: The convergent total synthesis of (+)-xestodecalactone A ( ) is reported. In addition, a formal synthesis of (+)-sporostatin has been accomplished by means of intercepting a previously reported intermediate en route to . The key reaction utilized was a convergent Pd-catalyzed α-arylation between a boronic acid and an α-bromoester.
    Keywords: Allylation ; Reduction ; Natural Products ; Cross-Metathesis ; Caylobolide ; Chemistry
    ISSN: 0040-4039
    E-ISSN: 1873-3581
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  • 8
    Language: English
    In: Proceedings of the National Academy of Sciences of the United States of America, 25 June 2013, Vol.110(26), pp.10794-9
    Description: Staphylococcus aureus causes diseases ranging from superficial wound infections to more invasive manifestations like osteomyelitis and endocarditis. The evasion of host phagocytes recruited to the site of infection is essential to the success of S. aureus as a pathogen. A single S. aureus strain can produce up to five different bicomponent pore-forming leukotoxins that lyse immune cells by forming pores in the cellular plasma membrane. Although these leukotoxins have been considered redundant due to their cytotoxic activity toward human neutrophils, each toxin displays varied species and cell-type specificities. This suggests that cellular factors may influence which cells each toxin targets. Here we describe the identification of CD11b, the α subunit of the αM/β2 integrin (CD11b/CD18), macrophage-1 antigen, or complement receptor 3, as a cellular receptor for leukocidin A/B (LukAB), an important toxin that contributes to S. aureus killing of human neutrophils. We demonstrate that CD11b renders human neutrophils susceptible to LukAB-mediated killing by purified LukAB as well as during S. aureus infection ex vivo. LukAB directly interacts with human CD11b by binding to the I domain, a property that determines the species specificity exhibited by this toxin. Identification of a LukAB cellular target has broad implications for the use of animal models to study the role of LukAB in S. aureus pathogenesis, explains the toxin's tropism toward human neutrophils and other phagocytes, and provides a cellular therapeutic target to block the effect of LukAB toward human neutrophils.
    Keywords: Pore-Forming Cytotoxin ; Toxin Receptor ; Bacterial Toxins -- Immunology ; Cd11b Antigen -- Metabolism ; Leukocidins -- Immunology ; Neutrophils -- Immunology ; Staphylococcus Aureus -- Pathogenicity
    ISSN: 00278424
    E-ISSN: 1091-6490
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  • 9
    Language: English
    In: Tetrahedron Letters, June 3, 2015, Vol.56(23), p.3057(3)
    Description: To link to full-text access for this article, visit this link: http://dx.doi.org/10.1016/j.tetlet.2014.11.030 Byline: Aymara M.M. Albury, Dripta De Joarder, Michael P. Jennings Abstract: Display Omitted Article History: Received 20 October 2014; Revised 5 November 2014; Accepted 6 November 2014
    ISSN: 0040-4039
    Source: Cengage Learning, Inc.
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  • 10
    Language: English
    In: The Journal of organic chemistry, 07 September 2012, Vol.77(17), pp.7688-92
    Description: The total synthesis of 7-deoxy-6-O-methylfusarentin (1) and a formal synthesis of 7-deoxy-6,8-O-dimethylfusarentin (2) has been successfully achieved in 10 steps. The described tactic underscores a diastereoselective strategy which incorporates a single acyclic reaction based on the initial stereocenter by means of a 1,3-chelation-controlled Reetz-Keck-type allylation.
    Keywords: Alcohols -- Chemistry ; Alkenes -- Chemistry ; Chromones -- Chemical Synthesis
    ISSN: 00223263
    E-ISSN: 1520-6904
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