Study toward the total synthesis of lysicamine: an aporphine alkaloid with antileishmanial activity

Study toward the total synthesis of lysicamine: an aporphine alkaloid with antileishmanial activity

Muraca, Ana Carolina A.; Raminelli, Cristiano

Abstract:

Benzyne can be considered a highly reactive intermediate with application in reactions of insertion into sigma bonds and also in cycloaddition reactions, which have been broadly employed in total syntheses of bioactive natural products and in preparations of functional materials. Accordingly, we intend to accomplish the total synthesis of aporphine alkaloid named lysicamine (1), a compound with antileishmanial activity, employing strategy which has as key step the [4+2] cycloaddition reaction between 1-methylene-1,2,3,4- tetrahydroisoquinoline (3) and benzyne (7), generated from 2-(trimethylsilyl)phenyl triflate (8), under mild reaction conditions.

Benzyne can be considered a highly reactive intermediate with application in reactions of insertion into sigma bonds and also in cycloaddition reactions, which have been broadly employed in total syntheses of bioactive natural products and in preparations of functional materials. Accordingly, we intend to accomplish the total synthesis of aporphine alkaloid named lysicamine (1), a compound with antileishmanial activity, employing strategy which has as key step the [4+2] cycloaddition reaction between 1-methylene-1,2,3,4- tetrahydroisoquinoline (3) and benzyne (7), generated from 2-(trimethylsilyl)phenyl triflate (8), under mild reaction conditions.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201395203139

Referências bibliográficas

• [1] 1(a) Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550. (b) Gampe, C. M.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3766.
• [2] 2(a) Chen, Y.-L.; Wong, M.-S.; Wong, W.-Y.; Lee, A. W. M. Tetrahedron Lett. 2007, 48, 2421. (b) Guitián, E.; Pérez, D.; Peña, D. Top. Organomet. Chem. 2005, 14, 109.
• [3] 3(a) Atanes, N.; Castelo, L.; Guitián, E.; Saá, C.; Saá, J. M.; Suau, R. J. Org. Chem. 1991, 56, 2984. (b) Saá, C.; Guitián, E.; Castedo, L.; Saá, J. M. Tetrahedron Lett. 1985, 26, 4559.
• [4] 4Waechter, A. I.; Cavé, A.; Hocquemiller, R.; Bories, C.; Muñoz, V.; Fournet, A. Phytother. Res. 1999, 13, 175.
• [5] 5Singh, O. V.; Huang, W. J.; Chen, C. H.; Lee, S. S. Tetrahedron Lett. 2007, 48, 8166.

Como citar:

Muraca, Ana Carolina A.; Raminelli, Cristiano; "Study toward the total synthesis of lysicamine: an aporphine alkaloid with antileishmanial activity", p-114-114. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201395203139