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  • 1
    Digitale Medien
    Digitale Medien
    Bausteine für die Synthese von Indolalkaloiden: Stereoselektive Protonierung von Butyrolacton-Enolat (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 2027-2029 
    Details
    ISSN: 0009-2940
    Schlagwort(e): Indolo[2,3-a]quinolizine, stereoselective protonation ; Chemistry ; Inorganic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Building Block for the Synthesis of Indole Alkaloids: Stereoselective Protonation of Butyrolactone EnolateLithium butyrolactone enolate adds stereoselectively to pyridium salts 2 to form an intermediate for the indole alkaloid antirhine (1). The desired stereochemistry, determined by X-ray analysis, was obtained by a deprotonation-reprotonation step.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/cber.19891221034
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  • 2
    Digitale Medien
    Digitale Medien
    Alkylierung cyclischer α,β-ungesättigter Ketone an der Doppelbindung (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 385-390 
    Details
    ISSN: 0009-2940
    Schlagwort(e): Chemistry ; Inorganic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Alkylation of Cyclic α,β-Unsaturated Ketones at the Double BondThe alkylation of (+)-(1S,7aS)-1-tert-butoxy-1,2,3,6,7,7a-hexahydro-7a-methyl-5H-inden-5-one (1) at C-4 with homogeranyl bromide (2) or 3-methoxy- and 3,5-dimethoxyphenethyl tosylate or bromide (4a, b, 5a, b), resp., affords excellent yields of 3 and 6, 7, resp., if 1,2-dimethoxyethane is used as the solvent. Similarly 4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalinone (8) can be alkylated easily at C-4.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/cber.19801130137
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  • 3
    Digitale Medien
    Digitale Medien
    Highly Functionalized Bicyclo[3.2.1]octane Derivatives from Readily Available 2′-Alkoxytricyclo[3.2.1.02,7]octanes: Building Blocks for Terpenes, Part I (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 441-451 
    Details
    ISSN: 1434-193X
    Schlagwort(e): Cascade reaction ; Aprotic Michael reaction ; Tricyclo[3.2.1.02,7]octanes ; Bicyclo[3.2.1]octanes ; Deprotonated cyclopropanes ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: 2′-Alkoxytricyclo[3.2.1.02,7]octanes 4-R are obtained in good to excellent yields from methyl 2-chloro-2-cyclopropylideneacetate (3) and the dienolates derived from the 3-alkoxycyclohex-2-enones 1-R and 2-R, by a cascade of two consecutive Michael additions and a γ-elimination. Compounds 4-R are transformed to the correspondingly substituted bicyclo[3.2.1]octanecarboxylates 5 by treatment with acid. 2′-Methoxytricyclooctanes 4a-d-Me are readily deprotonated to give chelation-stabilized cyclopropyllithium derivatives 6-Me, which react with electrophiles to yield the 7′-substituted tricyclo[3.2.1.02,7]octanes 4f-i-Me (61-66%). By acidic workup of such reaction mixtures, or subsequent treatment of the isolated products 4f-i-Me with acid, efficient transformation to the correspondingly substituted bicyclo[3.2.1]octanecarboxylates 5 is observed.
    Materialart: Digitale Medien
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  • 4
    Digitale Medien
    Digitale Medien
    Synthese von (±)-2-Oxo-seychellen und (±)-2-Oxo-4-epi-seychellen (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 63-68 
    Details
    ISSN: 0170-2041
    Schlagwort(e): Michael addition, aprotic ; [2 + 2] Addition ; Bicyclo[2.2.2]octanes ; Tricyclo[5.3.1.03,8]undecanes ; Sesquiterpene synthesis ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Synthesis of (±)-2-Oxo-seychellene and (±)-2-Oxo-4-epi-seychelleneAprotic Michael additions, which generate the functionalized bicyclo[2.2.2]octane 8 from ethyl 2-methyl-2,3-butadienoate (10) and the lithium cyclohexadienolate 9a, are the key steps in the synthesis of 6 (and its 4-epimer). 6 was made from 8 in 10 steps. The alternative Diels-Alder reaction of 10 with the trimethylsiloxycyclohexadiene 9b gave exclusively the [2+2] adduct 14 as a 1:1 mixture of diastereomers.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.199019900110
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