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

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Total synthesis of (±)-Preussin from an α,β-unsaturated diazoketone via the Stevens rearrangement

Rosset, Isac G. ; Burtoloso, Antonio C. B. ;

Abstract:

Preussin is a pyrrolidine alkaloid that has been isolated from the fermentation broths of Aspergillus ochraceus and Preussia sp. This compound exhibits antifungal, antibacterial and antitumor properties with potent growth-inhibitory and apoptosis-inducing effects on human cancer cells. In this work, we employed the chemistry of α,β- unsaturated diazoketones and ammonium-ylides to synthesize (±)-Preussin 1 in just 3 steps from decanal as depicted in Scheme 1. The main transformation in the present strategy involves a stereoselective Stevens rearrangement from an ammonium ylide.

Abstract:

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Palavras-chave: Diazoketones, preussin, Stevens rearrangment,

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013915103157

Referências bibliográficas
  • [1] 1Schwartz, R. E.; Liesch, J.; Hensens, O.; Zitano, L.; Honeycutt, S.; Garrity,
  • [2] G.; Fromtling, R. A.; Onishi, J.; Monaghan, R. J. Antibiot. 1988, 41, 1774.
  • [3] 2Achenbach, T. V.; Slater, E. P.; Brummerhop, H.; Bach, T.; Müller, R.
  • [4] Antimicrob. Agents Chemother. 2000, 44, 2794–2801.
  • [5] 3Pinho, V. D.; Burtoloso, A. C. B. J. Org. Chem. 2011, 76, 289–29.
Como citar:

Rosset, Isac G.; Burtoloso, Antonio C. B.; "Total synthesis of (±)-Preussin from an α,β-unsaturated diazoketone via the Stevens rearrangement", p. 251 . 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_2013915103157

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