Preparation of New Magnesium Carbenoids Aiming Inhibitors of HIV-1 Protease Synthesis

Preparation of New Magnesium Carbenoids Aiming Inhibitors of HIV-1 Protease Synthesis

Nishimura, R. H. V.; Toledo, F. T.; Clososki, G. C.

Abstract:

Inhibitors of HIV-1 protease were developed to act specifically on this enzyme class, with high affinity and high complementarity to the catalytic site of the protein, intrinsically competing with the natural substrates. The (2S,3S)-N-Boc-3-amino-1,2-epoxy- 4-phenylbutane (1) and its diastereomer of configuration (2R,3S) (2) are key intermediates in the preparation of some important antiretroviral compounds such as saquinavir, amprenavir, atazanavir and lopinavir. Thus, in this work we have investigated a new method for the stereoselective preparation of these chiral intermediates using organomagnesium reagents complexed with lithium chloride.

Inhibitors of HIV-1 protease were developed to act specifically on this enzyme class, with high affinity and high complementarity to the catalytic site of the protein, intrinsically competing with the natural substrates. The (2S,3S)-N-Boc-3-amino-1,2-epoxy- 4-phenylbutane (1) and its diastereomer of configuration (2R,3S) (2) are key intermediates in the preparation of some important antiretroviral compounds such as saquinavir, amprenavir, atazanavir and lopinavir. Thus, in this work we have investigated a new method for the stereoselective preparation of these chiral intermediates using organomagnesium reagents complexed with lithium chloride.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013913171326

Referências bibliográficas

• [1] 1 Wensing, A. M. J.; van Maarseveen, N. M.; Nijhuis, M. Antivir. Res. 2010,
• [2] 85, 59.
• [3] 2 Beaulieu, P. L.; Wernic, D. J. J. Org. Chem. 1995, 90, 6696.
• [4] 3 Krasovskiy, A.; Knochel, P. Angew. Chem. Int. Ed. 2004, 79, 14.

Como citar:

Nishimura, R. H. V.; Toledo, F. T.; Clososki, G. C.; "Preparation of New Magnesium Carbenoids Aiming Inhibitors of HIV-1 Protease Synthesis", p-237-237. 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_2013913171326