- Litebamine N-homologues: Preparation and anti-acetylcholinesterase activity
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Litebamine N-homologues were easily prepared from laurolitsine, generally via three reaction steps (N-alkylation, solvolysis with 1 M NH4OAc under reflux, and the Mannich reaction) in more than 80% overall yield. Among the prepared compounds, N-propyl-, N-isobutyl-, and N-isopropylnorlitebamines exhibited moderate antiacetylcholinesterase activity (IC50 ca. 7.0 μM), while the corresponding N-metho salt of N-propylnorlitebamine showed potent activity (IC50 2.70 μM).
- Chiou, Chi-Ming,Kang, Jaw-Jou,Lee, Shoei-Sheng
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- Efficient One-Pot Synthesis of Tetrahydronaphtho[2,1-f]isoquinolines by Using Domino Pictet–Spengler/Friedel–Crafts-Type Reactions
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This study describes a facile and efficient one-pot method for the synthesis of a tetrahydronaphtho[2,1-f]isoquinoline alkaloid. An N-protected amino aldehyde biaryl substrate underwent domino Pictet–Spengler/Friedel–Crafts-type cyclization reactions to p
- Khunnawutmanotham, Nisachon,Sahakitpichan, Poolsak,Chimnoi, Nitirat,Techasakul, Supanna
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- First total syntheses of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines annoretine and litebamine
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We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler-Napieralski cyclization
- Pampín, M. Carme,Estévez, Juan C.,Estévez, Ramón J.,Suau, Rafael,Castedo, Luis
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p. 8057 - 8065
(2007/10/03)
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- A novel ring cleavage and recyclization of N-cyanomethyl-1,2,3,4-tetrahydroisoquinolinium methiodides: A biomimetic synthesis of litebamine
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Treatment of N-cyanomethyl-6-hydroxy-1,2,3,4-tetrahydroisoquinolinium methiodide (1) with NaOMe in MeOH caused C1-N fission and simultaneous recyclization to give 8-hydroxy-5-methoxymethyl-1,2,3,4-tetrahydroisoquinoline (2). By using of the rea
- Hara, Hiroshi,Kaneko, Ken-Ichi,Endoh, Masaki,Uchida, Hideharu,Hoshino, Osamu
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p. 10189 - 10204
(2007/10/04)
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- A facile semisynthesis of litEbamine, a novel phenanthrene alkaloid, from boldine via a biogenetical approach
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Litebamine was semisynthesized from boldine via a biogenetical approach. Main reactions include Von Braun reaction, exhaustive benzylation and Hofmann degradation in one pot, and the Mannich reaction.
- Lee,Lin,Chen,Wu,Chen
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p. 6309 - 6310
(2007/10/02)
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