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

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.

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.

Palavras-chave:

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-251-251. 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_2013915103157