Strategies for Total Synthesis of Pyrenophorin

Strategies for Total Synthesis of Pyrenophorin

Barbosa, Jaqueline Rosa C.; Victor, Mauricio Moraes

Abstract:

Molecules belonging to the medium and large size rings lactones have attracted considerable attention from synthetic chemists due to their interesting biological properties. Due these structural features and importance, we have accepted the challenging to prepare Pyrenophorin 1 (Figure 1), a symmetric sixteen-membered diolide isolated from Pyrenophora avenae which displays potent antifungal activity. In our synthetic strategy to obtain a half-part of this molecule, we did testing by using some methods of coupling between fragments 3 and 4 for reach the ester 2. Further early experiments to obtain a ring intermediate have been made by using Nozaki-Hiyama-Kishi reaction. This work shows our results in this direction.

Molecules belonging to the medium and large size rings lactones have attracted considerable attention from synthetic chemists due to their interesting biological properties. Due these structural features and importance, we have accepted the challenging to prepare Pyrenophorin 1 (Figure 1), a symmetric sixteen-membered diolide isolated from Pyrenophora avenae which displays potent antifungal activity. In our synthetic strategy to obtain a half-part of this molecule, we did testing by using some methods of coupling between fragments 3 and 4 for reach the ester 2. Further early experiments to obtain a ring intermediate have been made by using Nozaki-Hiyama-Kishi reaction. This work shows our results in this direction.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013102145639

Referências bibliográficas

• [1] 1 Ishibashi, K.; Agric. Chem. Soc. 1961, 35, 257.
• [2] 2 Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M.; Bull. Chem. Soc. Jpn. 1979, 52, 1989.
• [3] 3 Navarro, I.; Basset, J.-F.; Hebbe, S.; Major, S. M.; Werner, T.; Howsham, C.; Brackow, J.; Barrett, A. G. M.; J. Am. Chem. Soc. 2008, 130, 10293.
• [4] 4 Lee, D.; Yun, S.Y.; Hansen, E.C.; Vochkov, I.; Cho, E.J.; Lo, W.Y. Angew. Chem. Int. Ed. 2010, 49, 4263.

Como citar:

Barbosa, Jaqueline Rosa C.; Victor, Mauricio Moraes; "Strategies for Total Synthesis of Pyrenophorin", p-135-135. 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_2013102145639