Dezembro 2013 vol. 1 num. 2 - Brazilian Meeting on Organic Synthesis 2013

Abstract - Open Access.

Idioma principal

Studies Towards Asymmetric Total Synthesis of Populene D

Ishikawa, Eloisa E. ; Jr., Luiz F. Silva ;

Abstract:

Populene D (Figure 1) was isolated from the trunk of Thespesia populnea, as optically active, however its absolute configuration has not been assigned. Some biological activity tests were carried out with this compound and amongst, the activity against cervical cancer (HeLa) must be highlighted (IC50=0,95 g/mL). The synthesis of this natural product has not been reported. Herein, we show studies towards the asymmetric total synthesis of populene D, using as the key step an iodine-catalyzed Prins cyclization reaction (Figure 1).

Abstract:

Palavras-chave: Populene D, π-Allylic Complex, Total Synthesis.,

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013913144428

Referências bibliográficas
  • [1] 1 Boonsri, S.; Karalai, C.; Ponglimanont, C.; Chantrapromma, S.; Kanjana-opas, A. J. Nat. Prod. 2008, 71, 1173.
  • [2] 2 Silva, L. F.Jr.; Quintiliano, S. A. P. Tetrahedron Lett. 2009, 50, 2256.
  • [3] 3 Mc Nulty, J.; Mao, J. Tetrahedron Lett. 2002, 43, 3857.
  • [4] 4 Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180.
  • [5] 5 Annunziata, R.; Cinquini, M.; Cozzi, F.; Dondio, G.; Raimondi, L. Tetrahedron 1987, 43, 2369.
  • [6] 6 Chow, R.; Kocienski, P.J.; Kuhl, A.; LeBrazidec, J. Y.; Muir, K.; Fish, P.; J. Chem. Soc., Perkin Trans. 1 2001, 43, 2344.
  • [7] 7 Burnell, R. H.; Jean, M.; Poirier, D. Can. J. Chem. 1987, 65, 775.
  • [8] 8 Ferraz, H. M. C.; Silva, L. F., Jr. Tetrahedron 2001, 57, 9939.
  • [9] 9 Ikeda, I.; Kanematsu, K. J. Chem. Soc., Chem. Commun. 1 1995, 4, 453.
Como citar:

Ishikawa, Eloisa E.; Jr., Luiz F. Silva; "Studies Towards Asymmetric Total Synthesis of Populene D", p. 230 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-15bmos-BMOS2013_2013913144428

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