Organic Process Research and Development p. 270 - 283 (2016)
Update date:2022-08-03
Topics:
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
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.
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