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  • 1
    Electronic Resource
    Electronic Resource
    Solanum alkaloids. 132For Part 131, see Le thi Quyen, G. Adam and K. Schreiber, Liebigs Ann. Chem. 1143 (1994). - Electron impact mass spectrometry of solanidane N-oxides (1995)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 30 (1995), S. 201-205 
    Details
    ISSN: 1076-5174
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The electron impact mass spectra of nine solanidane N-oxides show, in addition to the known typical fragmentation pattern of the solanidane moiety, the fragment ions [M - C5H9]+ and [C6H12NO]+, due to thermal Cope syn-eliminations caused by the N-oxide function and subsequent cleavage of the bonds between C(22) and C(23) and between C(20) and C(22), respectively, in the so-obtained cyclic N,N-dialkylhydroxylamines.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jms.1190300130
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  • 2
    Electronic Resource
    Electronic Resource
    Solanum Alkaloids, 139 - Photolysis of N-Chlorospirosolanes (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1589-1592 
    Details
    ISSN: 0947-3440
    Keywords: Photolysis ; N-Chlorospirosolanes, photolysis of ; 23-Chloro- and 23,23-dichlorospirosolanes ; Steroids ; Alkaloids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: UV irradiation of N-chlorosoladulcidine (2) in trifluoroacetic acid, followed by separation and hydrolysis of the obtained 3-O-trifluoroacetates affords (23R)-23-chlorosoladulcidine (5) and 23,23-dichlorosoladulcidine (7). Similar treatment of N-chlorotomatidine (9) affords 23,23-dichloro-22-isotomatidine (12).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970741
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  • 3
    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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  • 4
    Electronic Resource
    Electronic Resource
    Partial Synthesis of Nitrogenous Brassinosteroid Analogues with 22,26-Epiminocholestane and Spirosolane Skeleton (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 1143-1147 
    Details
    ISSN: 0170-2041
    Keywords: Bassinosteroids ; Steroids ; Alkaloids ; Solasodine ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Starting with the known (22S,25R)-16β-acetoxy-N-acetyl-22,26-epiminocholest-5-en-3β-ol (4), which has been prepared from the Solanum steroid alkaloid solasodine (3), we synthesized the nitrogenous brassinosteroid analogues (22S,25R)-2α,3α,16β-trihydroxy-22,26-epimino-5α-cholestan-6-one (11), (25R)-2α,22α-dihydroxy-5α,22αN-spirosolan-6-one (13), (22S,25R)-2α,3α,16β-trihydroxy-22,26-epimino-6,7-seco-5α-cholestano-6,7-lactone (15), and (25R)-2α-3α-dihydroxy-6,7-seco-5α,22αN-spirosolano-6,7-lactone (18) as well as some of their derivatives.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419941115
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  • 5
    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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