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  • π-Facial diastereoselectivity  (2)
  • 1,2,4-Triazines / Dienophiles, side-chain / [4+21 Cycloaddition / Pyrido[2,3-e-l,4-diazepines / Pyrido[2,3-b]-1,5-diazocines  (1)
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  • 1
    Electronic Resource
    Electronic Resource
    Synthese von Sieben- und Achtring-anellierten Pyridinen durch “inverse” intramolekulare Diels-Alder-Reaktion mit Trifluormethyl-substituierten 1,2,4-Triazinen (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 133-136 
    Details
    ISSN: 0009-2940
    Keywords: 1,2,4-Triazines / Dienophiles, side-chain / [4+21 Cycloaddition / Pyrido[2,3-e-l,4-diazepines / Pyrido[2,3-b]-1,5-diazocines ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of Seven- and Eight-Membered Ring-Annulated Pyridines by “Inverse” Intramolecular Diels-Alder Reaction with Trifluoromethyl-Substituted 1,2,4-TriazinesIntramolecular [4 + 2] cycloaddition reactions with inverse electron demand of trifluoromethyl-substituted 1,2,4-triazines carrying 7- or 8-membered o-alkyne side-chain dienophiles (3,8,12) lead to the synthesis of bicyclic pyridines with annulated heterocyclic seven- (5, 9, 13-15) or eight-membered rings (19, 22, 23, 26).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230125
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    (-)-(M,7S)-Colchicine and (-)-(M,7S)-10-Ethylthiocolchicide/Alkyne Cycloaddition Reactions: Synthesis of Novel Colchicine Derivatives by Consecutive [4+2] and [3+2] Cycloadditions (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 2451-2460 
    Details
    ISSN: 1434-193X
    Keywords: Colchicine ; 10-Ethylthiocolchicide, diene properties of ; π-Facial diastereoselectivity ; Consecutive [4+2],[3+2] cycloadditions ; Atropisomerism ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cycloaddition reactions of the facially dissymmetric diene moiety of (-)-(M,7S)-colchicine (5) and (-)-(M,7S)-10-ethylthiocolchicide (9) to various alkynes have been studied. With 5 and the dienophilic benzyne (3), dimethyl acetylenedicarboxylate (DMAD) (4) and cyclooctyne (6) as starting materials all cycloadditions could be realized with high regioselectivity at the 8,12-positions of the alkaloid. The approach of the dienophiles preferentially occurred toward the syn π-face of the diene. In contrast to the cycloaddition mode of 5 the ethylthiocolchicide 9 surprisingly reacted in a different manner. With benzyne as starting material a novel [3+2] cycloaddition of the thioenol ether moiety of 9 towards the dipolarophilic benzyne is supposed, affording the unexpected colchicide 10 after [1,5]H shift of the primarily formed cycloadduct followed by cleavage of the C-S linkage. With DMAD (4) and cyclooctyne (6) the reaction course is more complex. In a consecutive [4+2]/[3+2] cycloaddition (or vice versa) followed by a thermally induced cycloreversion of a not identified intermediate DMAD (4) gives rise to the polycyclic thiophene derivative 13 and the novel allocolchicinoid 14. In a similar way cyclooctyne (6) yielded three products, the thiophene-annulated homobarrelenones 18 and 19 and the tetracyclic allocolchicinoid 21. The structures of the novel colchicine derivatives were assigned on the basis of spectral data, those of the cycloadducts 1 and 19 were verified by X-ray crystallography. For the unprecedented formation of the various allocolchicinoids by consecutive [4+2]/[3+2] cycloadditions plausible reaction pathways are suggested, as far as possible. In addition the inhibitory effects on the tubulin polymerization reaction in vitro of 10, 14, and 21 are reported.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 3
    Electronic Resource
    Electronic Resource
    Positional and Facial Selectivity in Diels-Alder Reactions of (-)-(aS,7S)-Colchicine: Synthesis of Novel Analogues of the Alkaloid (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 851-857 
    Details
    ISSN: 0947-3440
    Keywords: Colchicine, diene properties of ; Positional selectivity ; Stabilized exciplex through hydrogen bonding ; π-Facial diastereoselectivity ; Photooxygenation ; Solvent effects ; Cycloadditions ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Positional and facial selectivity in Diels-Alder reactions of several hetero- and carbodienophiles with (-)-(aS,7S)-colchicine (1) has been examined. In all cases, cycloaddition occurred with high positional selectivity at the 8,12-positions of the alkaloid and preferentially from the diene face syn to the allylic substituent at the stereogenic center C-7. The observed high π-facial diastereoselectivity is independent of the polarity of the solvent used and is therefore probably a consequence of steric factors. The structures of the Diels Alder-adducts of 1 with singlet oxygen, N-phenyl-1,2,4-triazolinedione (PTAD) and trans-cyclooctene, 4,5, and 15, respectively, were assigned on the basis of spectral data and verified by X-ray crystallography.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970510
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    Paper (German National Licenses)
    Fulltext
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