Towards the Total Synthesis of Aerucyclamide B

Towards the Total Synthesis of Aerucyclamide B

Peña, Stella; Scarone, Laura; Serra, Gloria

Abstract:

Aerucyclamides A, B, C and D were isolated from the cyanobacteria Microcystis aeruginosa PCC 7806. Aerucyclamide B (1), Figure 1, shows the highest biological activity of the four against Plasmodium falciparum. This compound class encompasses hexacyclopeptides alternating in hydrophobic and hydrophilic (Ser, Thr, and Cys) amino acids. The side chains of these polar amino acids are heterocyclized to form oxazole or thiazole rings or their reduced derivatives. As part of our search for antiparasitic agents, in the present work we report the results towards the total synthesis of Aerucyclamide B.

Aerucyclamides A, B, C and D were isolated from the cyanobacteria Microcystis aeruginosa PCC 7806. Aerucyclamide B (1), Figure 1, shows the highest biological activity of the four against Plasmodium falciparum. This compound class encompasses hexacyclopeptides alternating in hydrophobic and hydrophilic (Ser, Thr, and Cys) amino acids. The side chains of these polar amino acids are heterocyclized to form oxazole or thiazole rings or their reduced derivatives. As part of our search for antiparasitic agents, in the present work we report the results towards the total synthesis of Aerucyclamide B.

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DOI: 10.5151/chempro-14bmos-R0068-1

Referências bibliográficas

• [1] 1a) Portmann, C.; Blom, J. F.; Gademann, K.; Jüttner, F. J. Nat. Prod. 2008, 71, 1193. b) Portmann, C., Blom, J. F., Kaiser, M., Brun, R., Jüttner, F. Gademann, K. J. Nat. Prod. 2008, 71, 1891.
• [2] 2 a) Sellanes, D.; Campot, F.; Nuñez, I.; Lin, G.; Espósito, P.; Saldaña, J.; Domínguez, L.; Manta, E.; Serra, G. Tetrahedron 2010, 66, 5384. b) Scarone, L.; Fajardo, J.; Saldaña, J.; Domínguez, L.; Espósito, P.; Dematteis, S.; Wipf, P.; Manta, E.; Serra, G. Lett. Drug, Des. And Disc. 2009, 6, 413.
• [3] 3 Phillips, A.J.; Yoshikazi, U.; Wipf, P.; Reno, M.J.; Williams, D.R. Org Lett. 2000, 2, 1165.
• [4] 4 Wipf, P.; Miller, C. P.; Venkatraman, S.; Fritch, P. C. Tetrahedron Lett. 1995, 36, 6395.

Como citar:

Peña, Stella; Scarone, Laura; Serra, Gloria; "Towards the Total Synthesis of Aerucyclamide B", p-68-68. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0068-1