6901-16-2Relevant academic research and scientific papers
Extremely facile formation of the pavine alkaloid skeleton by the photoreaction between isoquinoline and benzyltrifluoroborate
Nishigaichi, Yutaka,Ohmuro, Yuuki,Hori, Yoshiki,Ohtani, Takuya
supporting information, p. 118 - 120 (2020/02/25)
Appling the photo-benzylation of isoquinoline with benzyltrifluoroborate, an extremely facile method for the construction of a pavine alkaloid skeleton was developed. When 3-methoxybenzylboron reagents were employed to the reaction, it was found that not
An Enantioselective Access to 1-Alkyl-1,2,3,4-tetrahydroisoquinolines. Application to a New Synthesis of (-)-Argemonine
Youte, Jean-Jacques,Barbier, Denis,Al-Mourabit, Ali,Gnecco, Dino,Marazano, Christian
, p. 2737 - 2740 (2007/10/03)
Potassium ferricyanide oxidation of salt 1 gave isoquinolinone 7 whose treatment with Grignard reagents resulted in a high-yield formation of substituted isoquinolinium salts 5. The selectivity of the reduction of these salts to give derivatives 6 has been studied. Particularly good selectivities (82-84%) were observed when R is a benzylic group. On the basis of these results, a practical and enantioselective synthesis of the natural alkaloid (-)-argemonine is presented.
A new regioselective synthesis of isopavine and pavine alkaloids via double cyclization of N-(1,2-diarylethyl)-N-(2-phenylsulfinylethyl)formamide
Shinohara, Tatsumi,Takeda, Akira,Toda, Jun,Sano, Takehiro
, p. 981 - 992 (2007/10/03)
Pummerer reaction of N-[1,2-(3,4-dimethoxyphenyl)ethyl]-N-(2-phenylsulfinylethyl)formamide (9) using trifluoroacetic anhydride and boron trifluoride etherate caused double cyclization to give N-formylisopavine (21). Acid catalyzed cyclization of the 1,2-dihydroisoquinoline (23) prepared from 4-phenylthio-1,2,3,4-tetrahydroisoquinoline (11) gave N-formylpavine (26). LiAlH4 reduction of the N-formates (21 and 26) gave (±)-O-methylthalisopavine (4) and (±)-argemonine (5), respectively.
A novel asymmetric route to the 1,3-disubstituted tetrahydroisoquinoline, (-)-argemonine
Munchhof, Michael J.,Meyers
, p. 4607 - 4610 (2007/10/03)
Chiral bicyclic lactam 13 was converted to the natural product (-)-argemonine 9 in six steps. This novel route to argemonine represents a general strategy for the preparation of chiral 1,3-disubstituted tetrahydroisoquinolines.
Synthesis and reactions of N,N-bis[1-(trimethylsiloxy)alkyl]-formamides: Preparation of (±)-argemonine and (±)-norargemonine
Johnson, A. Peter,Luke, Richard W. A.,Singh, Gurmaj,Boa, Andrew N.
, p. 907 - 913 (2007/10/03)
Symmetrical and unsymmetrical N,N-bis[1-(trimethylsiloxy)alkyl]formamides are prepared and their reactions investigated, including an application to the synthesis of the pavine alkaloids (±)-argemonine and (±)-norargemonine.
Pavinan and Isopavinan Alkaloids. Synthesis of Racemic and Natural Thalidine, Bisnorargemonine, and Congeners from N-Norreticuline
Rice, Kenner C.,Ripka, W. C.,Reden, J.,Brossi, A.
, p. 601 - 607 (2007/10/02)
The isopavinan alkaloids thalidine and O-methylthalisopavine and the pavinan alkaloids bisnorargemonine and argemonine were synthesized as the racemates and natural isomers from the appropriate form of N-norreticuline.The sequence utilizing (S)-(-)-N-norr
