Substrate-controlled Asymmetric Morita-Baylis-Hillman Reaction: an Approach to the Synthesis of Pyrrolizidinones and Pyrrolizidines

Substrate-controlled Asymmetric Morita-Baylis-Hillman Reaction: an Approach to the Synthesis of Pyrrolizidinones and Pyrrolizidines

Scaramal, João P. S.; Luna-Freire, Kristerson R.; Coelho, and Fernando

Abstract:

The hexahydro-pyrrolizidine skeleton is a structural motif found in several biologically active compounds. The pyrrolizidinic alkaloids are a good example of compounds isolated from natural sources which exhibited this motif in their structures and remarkable biological effects. The biological relevance of these compounds justifies the development of new approach to them. We disclose herein a facile and fast approach to the synthesis of poly-hydroxylated pyrolizidinones and pyrrolizidines using Morita-Baylis-Hillman adducts as substrate.

The hexahydro-pyrrolizidine skeleton is a structural motif found in several biologically active compounds. The pyrrolizidinic alkaloids are a good example of compounds isolated from natural sources which exhibited this motif in their structures and remarkable biological effects. The biological relevance of these compounds justifies the development of new approach to them. We disclose herein a facile and fast approach to the synthesis of poly-hydroxylated pyrolizidinones and pyrrolizidines using Morita-Baylis-Hillman adducts as substrate.

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DOI: 10.5151/chempro-15bmos-BMOS2013_20131014152540

Referências bibliográficas

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• [3] 2 Luna-Freire, K. R.; Tormena, C. F.; Coelho, F. Synlett 2011, 2059-2063
• [4] urtis, M. D.; Shiu, K.; Butler, W. M. e Huffmann, J. C. J. Am. Chem. Soc.
• [5] 1986, 108, 3335.

Como citar:

Scaramal, João P. S.; Luna-Freire, Kristerson R.; Coelho, and Fernando; "Substrate-controlled Asymmetric Morita-Baylis-Hillman Reaction: an Approach to the Synthesis of Pyrrolizidinones and Pyrrolizidines", p-304-304. 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_20131014152540