Study toward the convergent total synthesis of the aporphine alkaloid PO-3

Study toward the convergent total synthesis of the aporphine alkaloid PO-3

Rossini, Allan F. C.; Raminelli, Cristiano

Abstract:

Due to the great importance of benzyne as a highly reactive intermediate in organic chemistry, with applications in total syntheses and in preparations of functional materials, we intend to accomplish the convergent total synthesis of the aporphine alkaloid PO-3 (1), a natural dye of green color, employing as key reaction a [4+2] cycloaddition between 1-methylene-1,2,3,4-tetrahydroisoquinoline (3) and the benzyne derivative 7, formed from 2-(trimethylsilyl)aryl triflate (8), under mild reaction conditions.

Due to the great importance of benzyne as a highly reactive intermediate in organic chemistry, with applications in total syntheses and in preparations of functional materials, we intend to accomplish the convergent total synthesis of the aporphine alkaloid PO-3 (1), a natural dye of green color, employing as key reaction a [4+2] cycloaddition between 1-methylene-1,2,3,4-tetrahydroisoquinoline (3) and the benzyne derivative 7, formed from 2-(trimethylsilyl)aryl triflate (8), under mild reaction conditions.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201392135541

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) Lu, X.; Nikawa, H.; Tsuchiya, T.; Akasaka, T.; Toki, M.; Sawa, H.; Mizorogi, N.; Nagase, S. Angew. Chem., Int. Ed. 2010, 49, 594. (b) Shen, Y.-M.; Grampp, G.; Leesakul, N.; Hu, H.-W.; Xu, J.-H. Eur. J. Org. Chem. 2007, 3718.
• [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] 4Singh, O. V.; Huang, W.-J; Chen, C.-H.; Lee, S.-S. Tetrahedron Lett. 2007, 48, 8166.

Como citar:

Rossini, Allan F. C.; Raminelli, Cristiano; "Study toward the convergent total synthesis of the aporphine alkaloid PO-3", p-106-106. 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_201392135541