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  • 1
    Electronic Resource
    Electronic Resource
    Solanum alkaloids, 117. Synthesis of the steroid alkaloid soladunalinidine and other 5α-spirosolan-3-amines (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 519-524 
    Details
    ISSN: 0170-2041
    Keywords: Soladunalinidine ; 5α-Tomatidan-3β-amine ; 5α-Solasodan-3α-amine and -3β-amine ; 5α-Spirosolan-3-amines ; Solanum steroid alkaloids ; Steroids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The steroid alkaloid soladunalinidine [5α-tomatidan-3β-amine, (25S)-5α,22βN-spirosolan-3β-amine, 2], isolated from Solanum dunalianum, is synthesized from tomatidine (5α-tomatidan-3β-ol, 1) via 5α-tomatidan-3-one (4) and its oxime 5 which is reduced to 2 as well as to its ring-E-opened (22S) and (22R) dihydro products 6 and 9, the N(22,26)-chloro-N(3)-(2-hydroxy-benzylidene) derivatives 8 and 11 of which are recyclized to N(3)-(2-hydroxybenzylidene)soladunalinidine (3). The 5α-spirosolan-3-amines stereoisomeric at C-22 and C-25, 5α-solasodan-3α-amine (13) and -3β-amine (15), are obtained in an analogous sequence of reactions from soladulcidine (5α-solasodan-3β-ol, 12).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199019900199
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  • 2
    Electronic Resource
    Electronic Resource
    Solanum Alkaloids, 126. Degradation of Solasodine to 16β,22-Epoxy-23,24-dinorchol-5-ene-3β,22β-diol and Partial Synthesis of (23s)-23-Hydroxysolasodine (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 167-172 
    Details
    ISSN: 0170-2041
    Keywords: Solasodines ; Chol-5-ene-3β,22β-diol, 16β,22-epoxy-23,24-dinor- ; Solanum steroid alkaloids ; Steroids ; Alkaloids ; Ruschig reaction ; Grob fragmentation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (22R,23S,25R)-N-Chloro-22,26-epiminocholest-5-ene-3β,16β,23-triol (11) and its 3,16,23-O-triacetyl derivative 15 were prepared from solasodine (1). Treatment of 11 or 15 with sodium methanolate yielded the 22,23-secoaldehyde 16 as major product (Grob fragmentation) and (23S)-23-hydroxysolasodine (2) as minor product (Ruschig reaction). Hydrolysis of 16 with methanolic hydrochloric acid afforded 16β,22-epoxy-23,24-dinorchol-5-ene-3β,22β-diol (17) and its 22-O-methyl derivative 18, the 3-O-acetate 19 of which was oxidized to the known acetyldiosgenin lactone (20), thus confirming the structures of 16-19. Compound 2 was shown to be identical in every respect with a rare spirosolane alkaloid, recently isolated from some Solanum species. Photolysis of (22R,23S,25R)-3β,16β-diacetoxy-N-chloro-22,26-epiminocholest-5-en-23-ol (10) yielded also via 22,23-carbon-carbon cleavage (20S)-3β,16β-diacetoxypregn-5-ene-20-carbaldehyde (21) as major product, which was converted by treatment with methanolic hydrochloric acid into the compound 18.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930130
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  • 3
    Electronic Resource
    Electronic Resource
    Solanum alkaloids, 121. Partial Synthesis of the Steroid Alkaloids Teinemine, 22-Isoteinemine, Etioline, and 25-Isoetioline (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 143-149 
    Details
    ISSN: 0170-2041
    Keywords: Teinemine and 22-isoteinemine ; Etioline and 25-isoetioline ; Solanum steroid alkaloids ; Steroids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The rare 16α-hydroxylated steroid alkaloids teinemine [(22S,25S)-22,26-epiminocholest-5-ene-3β,16α-diol, 8], 22-isoteinemine [(22R,25S)-22,26-epiminocholest-5-ene-3β,16α-diol, 10], etioline [(25S)-22,26-epiminocholesta-5,22(N)-diene-3β,16α-diol, 12], and 25-isoetioline [(25R)-22,26-epiminocholesta-5,22(N)-diene-3β,16α-diol, 21] are synthesized from the abundant spirosolane alkaloids tomatid-5-en-3β-ol [(25S)-22βN-spirosol-5-en-3β-ol, 1] and solasodine [(25R)-22αN-spirosol-5-en-3β-ol, 15], respectively. The crucial stages of these syntheses are the conversions of 1 or 15 into the N-protected (22S,25S)-, (22R,25S)-, and (22S,25R)-22,26-epimino-3β-hydroxycholest-5-en-16-ones 6, 7, and 18 as well as their reductions with sodium/ 2-propanol to the 16α-hydroxy compounds teinemine (8), 22-isoteinemine (10), and (22S,25R)-22,26-epiminocholest-5-ene-3β,16α-diol (19), respectively. By treatment with sodium methanolate the N-chloro derivatives 9 and 11 of 8 and 10 afford etioline (12). In an analogous manner, the N-chloro derivative 20 of 19 is converted into 25-isoetioline (21).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199119910126
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