- TWO STEROIDAL ALKALOIDS, HAPEPUNINE AND ANRAKORININE, FROM THE MATURE FRITILLARIA CAMTSCHATCENSIS
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Key word Index - Fritillaria camtschatcensis; Liliaceae; N-methyl-22,26-epiminocholestene; spirosolane. After acid hydrolysis of a glycosidic fraction from aerial parts of Fritillaria camtschatcensis, in addition to solanidine, tomatidenol, and solasodine, two N-methyl-22,26-epiminocholestenes, hapepunine and anrakorinine, were isolated and their structures elucidated by physical and chemical methods.
- Kaneko,Ko,Nakaoka, Utako,Tanaka, Mikako,Yoshida, Naotoshi,Mitsuhashi, Hiroshi
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Read Online
- Solanum Alkaloids, 124, Preparation of N-Hydroxyspirosolane Alkaloids
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The N-Hydroxyspirosolane alkaloids N-hydroxysolasodine (1) and N-hydroxytomatidine (10) as well as the N-hydroxy-22,26-epiminocholestene 7 have been prepared by oxidation of the respective amines 2, 11, and 5 with hydrogen peroxide in the presence of selenium dioxide.Key Words: Solasodines / Tomatidines / Alkaloids / Solanum steroid alkaloids / Spirosolanes / Steroids
- Ripperger, Helmut
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p. 1091 - 1094
(2007/10/02)
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- Partial Synthesis of the Steroid Alkaloids Teinemine, 22-Isoteinemine, Etioline, and 25-Isoetioline
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The rare 16α-hydroxylated steroid alkaloids teinemine , 22-isoteinemine , etioline , and 25-isoetioline are synthesized from the abundant spirosolane alkaloids tomatid-5-en-3β-ol and solasodine , respectively.The crucial stages of these syntheses are the conversion 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).
- Quyen, Le thi,Ripperger, Helmut,Schreiber, Klaus
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p. 143 - 149
(2007/10/02)
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