A New Method of Spiroketalization via Cascade Oxidative Dearomatization

A New Method of Spiroketalization via Cascade Oxidative Dearomatization

Shirley, Harry J.; Bray, Christopher D.

Abstract:

Spiroketals have been isolated from an array of sources in Nature such as insects, bacteria and marine organisms. The intriguing and often potent bioactivity of many spiroketal containing natural products, e.g. 1 And 2, makes them frequent synthetic targets. Several high value pharmaceuticals, e.g. avermectin, contain a spiroketal motif. Many current methods for spiroketal formation do not lend themselves to the often architecturally challenging structures present in natural product targets. Thus the development of new methods for spiroketalization is of key importance for the synthesis of many biologically active natural products.

Spiroketals have been isolated from an array of sources in Nature such as insects, bacteria and marine organisms. The intriguing and often potent bioactivity of many spiroketal containing natural products, e.g. 1 And 2, makes them frequent synthetic targets. Several high value pharmaceuticals, e.g. avermectin, contain a spiroketal motif. Many current methods for spiroketal formation do not lend themselves to the often architecturally challenging structures present in natural product targets. Thus the development of new methods for spiroketalization is of key importance for the synthesis of many biologically active natural products.

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DOI: 10.5151/chempro-15bmos-BMOS2013_20138255339

Referências bibliográficas

• [1] 1. (a) Perron, F.; Albizati, K., Chem. Rev., 1989, 89, 1617. (b) Favre, S.; Vogel, P.; Gerber-Lemaire, S., Molecules, 13,
• [2] 2570.
• [3] 2. (a) Ohtake, Y.; Sato, T.; Kobayash, T.; Nishimoto, M.; Taka, N.; Takano, K.; Yamamoto, K.; Ohmori, M.; Yamaguchi,
• [4] M.; Takami, K.; Yeu, S.Y.; Ahn, KH.; Matsuoka, H.; Morikawa, K.; Suzuki, M.; Hagita, H.; Ozawa, K.; Yamaguchi, K.; Kato,
• [5] M.; Ikeda, S., J. Med. Chem, 2012, 55, 7828. (b) Reddy, C.; Srikanth, B.; Uredi, D.; Rao, K.V.M.; Jagadeesh, B., Eur. J. Org. Chem., 2012, 3, 525.
• [6] 3. For a review of dearomatization strategies see; (a) Roche, S.P.; Porco, J.A. Jr. Angew. Chem. Int. Ed., 2011, 50, 4068. For a review of cascade polycyclisations see; (b) Anderson, E. A. Org. Biomol. Chem., 2011, 9, 3997.

Como citar:

Shirley, Harry J.; Bray, Christopher D.; "A New Method of Spiroketalization via Cascade Oxidative Dearomatization", p-6-6. 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_20138255339