- N-BENZYLISOQUINOLINE ALKALOIDS FROM CERATOCAPNOS HETEROCARPA
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Three new N-benzylisoquinoline alkaloids, namely isosendaverine, capnosine and capnosinine, were isolated from Ceratocapnos heterocarpa in addition to the known sendaverine.Their structure was established by spectroscopic methods and verified by total synthesis.
- Suau, Rafael,Silva, M. Victoria,Ruiz, Inmaculada,Valpuesta, Maria
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p. 241 - 244
(2007/10/02)
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- A FACILE ROUTE TO TETRAHYDROISOQUINOLINE ALKALOIDS VIA SULFOXIDE MEDIATED CYCLIZATION
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A facile route to 1,2,3,4-tetrahydroisoquinoline framework has been developed by employing the sulfoxide mediated cyclization reaction.Utilizing the reaction developed some naturally occurring isoquinoline alkaloids have been synthesized.
- Takano, Seiichi,Iida, Hirokazu,Inomata, Kohei,Ogasawara, Kunio
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- Inverse Electron Demand Diels-Alder Reactions of 3-Carbomethoxy-2-pyrones. Controlled Introduction of Oxygenated Aromatics: Benzene, Phenol, Catechol, Resorcinol, and Pyrogallol Annulation. Regiospecific Total Synthesis of Sendaverine and a Preparation of 6,7-Benzomorphans
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A full investigation of the preparation and Diels-Alder reactions of 3-carbomethoxy-2-pyrones is described.Methods for the preparation of a full range of oxygen-substituted aromatics: benzene, 1-, 2-, or 3-phenol, symmetrical or unsymmetrical o-catechol, resorcinol, and pyrogallol annulation from a common 3-carbomethoxy-2-pyrone intermediate are detailed.A regiospecific total synthesis of sendaverine, a 2-benzyltetrahydroisoquinoline possessing a selectively protected, symmetrical o-catechol, and a preparation of 6,7-benzomorphans are described.
- Boger, Dale B.,Mullican, Michael D.
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p. 4033 - 4044
(2007/10/02)
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- A NOVEL ROUTE TO THE SYNTHESIS OF SUBSTITUTED N-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES. SYNTHESIS OF SENDAVERINE AND CORGOINE
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The condensation product of 2-aminoethanol with substituted benzaldehyde was reduced and N-benzylated with substituted benzyl chloride followed by PPA cyclization to obtain substituted N-benzyl-tetrahydroisoquinolines; likewise the condensation product of
- Masood, M.,Tiwari, K. P.
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p. 177 - 182
(2007/10/02)
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- A Novel Synthesis of the 2-Benzylisoquinoline Alkaloids, Sendaverine and Corgoine, with Aziridinium Salts as Reactive Intermediates
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A total synthesis of the 2-benzylisoquinoline alkaloids sendaverine (1) and corgoine (2) has been achieved by employing the ring-opening reaction of aziridinium salts as a key step.
- Otomasu, Hirotaka,Higashiyama, Kimio,Honda, Toshio,Kametani, Tetsuji
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p. 2399 - 2402
(2007/10/02)
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- AZIRIDINE IN ALKALOID SYNTHESIS : A NOVEL SYNTHESIS OF SENDAVERINE
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A facile synthesis of 2-benzylisoquinoline alkaloid, sendaverine, has been achieved by ring opening of aziridine derivative as a key reaction.
- Otomasu, Hirotaka,Higashiyama, Kimio,Honda, Toshio,Kametani, Tetsuji
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p. 353 - 355
(2007/10/02)
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- A New Total Synthesis of Sendaverine
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Ethyl 4-benzyloxy-2-bromomethyl-5-methoxyphenylacetate (3) on condensation with 4-methoxybenzylamine (4) in DMF in the presence of triethylamine gives 7-benzyloxy-6-methoxy-2-(4'-methoxybenzyl)-1,4-dihydro-3(2H)-isoquinolone (5).LAH reduction of 5 in THF, followed by debenzylation with ethanolic HCl, furnishes sendaverine (6).
- Pandey, G. D.,Tiwari, K. P.
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p. 160 - 161
(2007/10/02)
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