900811-38-3Relevant articles and documents
Convergent Synthesis of the Renin Inhibitor Aliskiren Based on C5-C6 Disconnection and CO2H-NH2 Equivalence
Cini, Elena,Banfi, Luca,Barreca, Giuseppe,Carcone, Luca,Malpezzi, Luciana,Manetti, Fabrizio,Marras, Giovanni,Rasparini, Marcello,Riva, Renata,Roseblade, Stephen,Russo, Adele,Taddei, Maurizio,Vitale, Romina,Zanotti-Gerosa, Antonio
, p. 270 - 283 (2016/03/04)
A novel synthesis of the renin inhibitor aliskiren based on an unprecedented disconnection between C5 and C6 was developed, in which the C5 carbon acts as a nucleophile and the amino group is introduced by a Curtius rearrangement, which follows a simultaneous stereocontrolled generation of the C4 and C5 stereogenic centers by an asymmetric hydrogenation. Operational simplicity, step economy, and a good overall yield makes this synthesis amenable to manufacture on scale.
Rhodium-catalyzed enantioselective hydrogenation of (E)-enol acetate acids
Arena, Giada,Barreca, Giuseppe,Carcone, Luca,Cini, Elena,Marras, Giovanni,Nedden, Hans G.,Rasparini, Marcello,Roseblade, Stephen,Russo, Adele,Taddei, Maurizio,Zanotti-Gerosa, Antonio
supporting information, p. 1449 - 1454 (2013/06/27)
The novel rhodium complex [Rh(S)-Phanephos(cod)]-catalyzed hydrogenation of disubstituted (E)-enol acetate carboxylic acids is reported. The catalytic cycle works under 30 bar of hydrogen under conventional heating giving different 3-acetoxy-2,3-disubstituted carboxylic acids with ee ≥90%. Hydrogenation occurred also under microwave dielectric heating without eroding the enantioselectivity but improving the overall efficiency of the process. With microwaves, hydrogen pressure and reaction time required for complete hydrogenation dropped to 5 bar and 30 min, respectively. The best performance of this catalyst under microwave irradiation was TON 100, TOF 196 h-1 with ee 99% on a 6-g scale. Copyright
CONVERGENT SYNTHESIS OF RENIN INHIBITORS AND INTERMEDIATES USEFUL THEREIN
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Page/Page column 26-27, (2009/07/25)
Described is a method for the preparation of renin inhibitors such as aliskiren, and intermediates useful therein. The method introduces a nitrogen-containing intermediate such as a lactone of formula (8). with R4 being a branched C3_6/su