Formal total synthesis of aliskiren

Chemistry : a European Journal
Byron K PetersPher G Andersson

Abstract

The efficient and selective formal total synthesis of aliskiren is described. Aliskiren, a renin inhibitor drug, has received considerable attention, primarily because it is the first of the renin inhibitor drugs to be approved by the FDA. Herein, the formal synthesis of aliskiren by iridium-catalyzed asymmetric hydrogenation of two allylic alcohol fragments is reported. Screening a number of N,P-ligated iridium catalysts yielded two catalysts that gave the highest enantioselectivity in the hydrogenation, which gave the saturated alcohols in 97 and 93 % ee. In only four steps after hydrogenation, the fragments were combined by using the Julia-Kocienski reaction to produce late-stage intermediate in an overall yield of 18 %.

References

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May 17, 2008·Journal of the American Chemical Society·Montserrat DiéguezPher G Andersson
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May 26, 2009·Journal of the American Chemical Society·Pradeep CherukuPher G Andersson
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Oct 8, 2009·Chemical Communications : Chem Comm·Alexander PaptchikhinePher G Andersson
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Apr 26, 2012·Chemistry : a European Journal·J Johan VerendelPher G Andersson
Jul 19, 2012·Chemistry : a European Journal·Jia-Qi LiPher G Andersson
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Feb 27, 2014·Chemical Reviews·J Johan VerendelPher G Andersson

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