Synthesis of (–)-(R)-angustureine by formal alkynylation of a chiral ß-amino ester

Synthesis of (–)-(R)-angustureine by formal alkynylation of a chiral ß-amino ester

Muñoz*, Gaspar Diaz; Dudley, Gregory B.

Abstract:

The South American angostura tree, Galipea officinalis Hancock, is one of the twenty species of the genus Galipea Aublet. In 1999, Jacquemond described the isolation of tetrahydroisoquinoline alkaloids including angustureine (1, Scheme 1) from the angostura tree bark; antimalarial and cytotoxic properties of this and congeneric alkaloids were later found. The promising biological activity of its alkaloid extracts, and a general interest in tetrahydroisoquinoline synthesis has led to considerable attention on angustureine from the synthetic community.

The South American angostura tree, Galipea officinalis Hancock, is one of the twenty species of the genus Galipea Aublet. In 1999, Jacquemond described the isolation of tetrahydroisoquinoline alkaloids including angustureine (1, Scheme 1) from the angostura tree bark; antimalarial and cytotoxic properties of this and congeneric alkaloids were later found. The promising biological activity of its alkaloid extracts, and a general interest in tetrahydroisoquinoline synthesis has led to considerable attention on angustureine from the synthetic community.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201372919131

Referências bibliográficas

• [1] 1 Jacquemond-Collet, I.; Bessiere, .-M.; Hannedouche, S.; Bertrand, C.; Fouraste, I.; Moulis, C.; Phytochemical Analysis 2001, 12, 312.
• [2] 2 Jacquemond-Collet, I.; Hannedouche, S.; Fabre, N., Fourasté, I.; Moulis, C.; Phytochemistry 1999, 51, 1167.
• [3] 3 Jacquemond-Collet, I.; Stanislas, E.; Mallié, M.; Planta Med. 2002, 68, 68.
• [4] 4 Nagata, R.; Tanno, N.; Kodo, T.; Ae, N.; Antoku, F.; Tatsuno, T.; Kato, T.; Yanaka, Y.; Nakamura, M.; J. Med. Chem. 1994, 37, 3956.

Como citar:

Muñoz*, Gaspar Diaz; Dudley, Gregory B.; "Synthesis of (–)-(R)-angustureine by formal alkynylation of a chiral ß-amino ester", p-38-38. 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_201372919131