Studies Toward the Total Synthesis of Seselidiol

Studies Toward the Total Synthesis of Seselidiol

Silva, Marcelo F. R.; Palmeira, Dayvson J.; Andrade, Leandro H.; Menezes, and Paulo H.

Abstract:

(±)-Seselidiol (Figure 1) a natural product isolated in 0.0085% yield from the roots of Seseli mairei Wolff (Umbelliferae) and used as herbal remedies for human inflammation, swelling, rheumatism, pain, and common cold in folk medicine. It also showed significant cytotoxicity in KB, P-388, and L-1210 tumor cells (ED50 20 μg/mL). The absolute stereochemistry of the stereogenic centers in Seselidiol is not known. Although its biological activity is known for over twenty years, due to date no total synthesis of the natural product has been attempted. These facts motivated us to propose a synthetic strategy for preparation.

(±)-Seselidiol (Figure 1) a natural product isolated in 0.0085% yield from the roots of Seseli mairei Wolff (Umbelliferae) and used as herbal remedies for human inflammation, swelling, rheumatism, pain, and common cold in folk medicine. It also showed significant cytotoxicity in KB, P-388, and L-1210 tumor cells (ED50 20 μg/mL). The absolute stereochemistry of the stereogenic centers in Seselidiol is not known. Although its biological activity is known for over twenty years, due to date no total synthesis of the natural product has been attempted. These facts motivated us to propose a synthetic strategy for preparation.

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DOI: 10.5151/chempro-14bmos-R0221-2

Referências bibliográficas

• [1] 1 Hu, C.-Q.; Chang, J.-J.; Lee, K.-H. J. Nat. Prod. 1990, 53, 932.
• [2] 2 Oliveira, J. M. ; Palmeira, D. J. ; Comasseto, J. V. ; Menezes. P. H. J. Braz. Chem. Soc. 2010, 21, 362-366
• [3] 3 Zeni, G., Comasseto, J. V. Tetrahedron Lett. 1999, 40, 4619.

Como citar:

Silva, Marcelo F. R.; Palmeira, Dayvson J.; Andrade, Leandro H.; Menezes, and Paulo H.; "Studies Toward the Total Synthesis of Seselidiol", p-221-221. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0221-2