Diversity synthesis of indolizidine alkaloids from a,b- unsaturated diazoketones by the Wolff rearrangement.

Diversity synthesis of indolizidine alkaloids from a,b- unsaturated diazoketones by the Wolff rearrangement.

Pinho, Vagner D.; Burtoloso, Antonio C. B.

Abstract:

Diazocarbonyl compounds are important reagents in organic synthesis. Among these reagents, a,b- unsaturated diazoketones have proven to be very promising as multi-functional intermediates, but they usually are difficult to prepare by common methods. Recently, we reported a general and straightforward methodology to prepare these important synthetic substrates and its application in the synthesis of pyrrolidine alkaloids (scheme1). Herein, we report another utility of these α,β-unsaturated diazoketones applying the Wolff rearrangement in the short synthesis of indolizidines alkaloids (Scheme 1).

Diazocarbonyl compounds are important reagents in organic synthesis. Among these reagents, a,b- unsaturated diazoketones have proven to be very promising as multi-functional intermediates, but they usually are difficult to prepare by common methods. Recently, we reported a general and straightforward methodology to prepare these important synthetic substrates and its application in the synthesis of pyrrolidine alkaloids (scheme1). Herein, we report another utility of these α,β-unsaturated diazoketones applying the Wolff rearrangement in the short synthesis of indolizidines alkaloids (Scheme 1).

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DOI: 10.5151/chempro-14bmos-R0128-1

Referências bibliográficas

• [1] 1Doyle, M. P.; McKervey, M. A.; Ye, T., Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, 1998
• [2] 2Pinho, V. D.; Burtoloso, A. C. B.; J. Org. Chem., 2011, 76, 289-292.
• [3] 3Kuhakarn, C.; Seehasombat, P.; Jaipetch, T.; Tetrahedron, 2008, 64, 1663-1670.
• [4] 4Lebrun, S.; Couture, A.; Deniau, E.; Grandclaudon, P.; Synthesis, 2008, 2771-2775.

Como citar:

Pinho, Vagner D.; Burtoloso, Antonio C. B.; "Diversity synthesis of indolizidine alkaloids from a,b- unsaturated diazoketones by the Wolff rearrangement.", p-128-128. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0128-1