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  • 2000-2004
  • 1990-1994  (3)
  • 1994  (3)
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  • 2000-2004
  • 1990-1994  (3)
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  • 1
    Electronic Resource
    Electronic Resource
    Radikalische Cyclisierung von Dienen, VIII. Über die regioselektive Herstellung von ungesättigten Cyclopenta[b]furan-2-onen aus (S)-(+)-Carvon  -  Bausteine zur Synthese von enantiomerenreinen Triquinanen (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 549-550 
    Details
    ISSN: 0009-2940
    Keywords: Radicals ; Cyclization ; Triquinanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Radical-Type Cyclization of Dienes, VIII[1].  -  On the Regioselective Synthesis of Unsaturated Cyclopenta[b]furan-2-ones from (S)-(+)-Carvone  -  Building Blocks for the Synthesis of Enantiomerically Pure TriquinanesThe diastereomeric products 2a and 2b, which were synthesized from (S)-(+)-carvone (1), are converted to (3aS,5S,6aS)-(-)-5-acetoxyhexahydro-6a-methyl-2H-cyclopenta[b]furan-2-one (4) in ca. 50% yield. 4 is regioselectively converted to (3aR,6aS)-(-)-3,3a,6,6a-tetrahydro-6a-methyl- (8a) and (3aS,6aR)-(+)-3,3a,4,6a-tetrahydro-6a-methyl-2H-cyclopenta[b]-furan-2-one (8b). These are used at the 10-g scale for the synthesis of enantiomerically pure triquinanes.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270314
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  • 2
    Electronic Resource
    Electronic Resource
    Radikalische Cyclisierung von Dienen, IX. Über die Stereoselektivität der radikalischen 4-exo-trig-Cyclisierung von optisch aktiven (2E)-6-Oxohex-2-ensäureestern mit Samarium(II)-iodid (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 1305-1309 
    Details
    ISSN: 0009-2940
    Keywords: Radicals ; Cyclobutanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Radical-Type Cyclization of Dienes, IX. - On the Stereoselectivity of the Radical 4-exo-trig-Cyclization of Optically Active Ethyl (2E)-6-Oxohex-2-enoates with Samarium(II) IodideEthyl (5R, 2E)-5-(benzyloxy)-4,4-dimethyl-6-oxohex-2-enoate (9) was prepared from (R)-(-)-pantolactone (3) by a series of straightforward reactions. The reaction of 9 with samarium(II) iodide produces enantiomerically pure ethyl (1S,3R,4R)-(-)-[3-(benzyloxy)-4-hydroxy-2,2-dimethylcyclo-butyl]acetate (10) in 60% yield. The absolute configuration at C-1 and C-3 was confirmed by the conversion of 10 to the crystalline 15a, whose absolute configuration is known from its synthesis from (1S,5S)-( + )-α-pinene (12). The configuration of the hydroxy group at C-4 in 10 was determined from NOE studies on the epimiric 17. The radical 4-exo-trig-cyclization of optically active (2E)-6-oxohex-2-enoates with samarium(II) iodide opens a new pathway to enantiomerically pure cyclobutanol and cyclobutanone derivatives, which are of interest as building blocks in natural products synthesis.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270720
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  • 3
    Electronic Resource
    Electronic Resource
    Synthese von (+)-Coriolin B aus (+)-Präcoriolin (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 99-101 
    Details
    ISSN: 0170-2041
    Keywords: (+)-Coriolin B ; Triquinans ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of (+)-Coriolin B from (+)-PrecoriolinEnantiomerically pure (3aS,3bR,4R,6aS,7S)-(+)-3,3a,4,5,6,6a,7-Octahydro-4,7-dihydroxy-3a,5,5-trimethyl-3-methylene 2H-cyclopenta[a]pentalen-2-one [(+)-precoriolin] (4), produced from (S)-(+)-carvone (3), is converted via the epoxides 5 and 7 into (+)-coriolin B (2).
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940117
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