A Two-Step Synthesis of the Bioprotective Agent JP4-039 from N-Boc-L-Leucinal.

A Two-Step Synthesis of the Bioprotective Agent JP4-039 from N-Boc-L-Leucinal.

Bernardim, Barbara; Burtoloso, Antonio C. B.

Abstract:

JP4-039 1 (scheme 1) is a novel nitroxide conjugate capable of crossing lipid bilayer membranes and scavenging reactive oxygen species (ROS). Only one synthesis is described in the literature, which consists of six steps and involves a one-pot hydrozirconation-transmetalation-addition to a chiral sulfinimine as the key step. As our group has been recently exploiting the chemistry of α,β-unsaturated diazoketones, we were interested in investigating these platforms for the direct synthesis of β,γ- unsaturated amides and apply the methodology to prepare the bioprotective agent JP4-039 in just one step from them.

JP4-039 1 (scheme 1) is a novel nitroxide conjugate capable of crossing lipid bilayer membranes and scavenging reactive oxygen species (ROS). Only one synthesis is described in the literature, which consists of six steps and involves a one-pot hydrozirconation-transmetalation-addition to a chiral sulfinimine as the key step. As our group has been recently exploiting the chemistry of α,β-unsaturated diazoketones, we were interested in investigating these platforms for the direct synthesis of β,γ- unsaturated amides and apply the methodology to prepare the bioprotective agent JP4-039 in just one step from them.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201391415657

Referências bibliográficas

• [1] 1 Frantz, M.C. et al. Org. Lett. 2011, 13, 2318–2321.
• [2] 2 Pinho, V. D.; Burtoloso, A. C. B. J. Org. Chem. 2011, 76, 289–292.
• [3] 3 Pinho, V. D.; Burtoloso, A. C. B. Tetrahedron Lett. 2012, 53, 876–878.
• [4] 4 Bernardim, B.; Pinho, V. D.; Burtoloso, A. C. B. J. Org. Chem. 2012, 77, 9926–9931.

Como citar:

Bernardim, Barbara; Burtoloso, Antonio C. B.; "A Two-Step Synthesis of the Bioprotective Agent JP4-039 from N-Boc-L-Leucinal.", p-79-79. 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_201391415657