A novel synthesis of the renin inhibitor aliskiren based on an unprecedented disconnection between C5 and C6 was developed, in which the CS 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.
Cini, E., Banfi, L., Barreca, G., Carcone, L., Malpezzi, L., Manetti, F., et al. (2016). Convergent Synthesis of the Renin Inhibitor Aliskiren Based on C5–C6 Disconnection and CO2H–NH2Equivalence. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 20(2), 270-283 [10.1021/acs.oprd.5b00396].
Convergent Synthesis of the Renin Inhibitor Aliskiren Based on C5–C6 Disconnection and CO2H–NH2Equivalence
CINI, ELENA;CARCONE, LUCA;MANETTI, FABRIZIO;TADDEI, MAURIZIO;
2016-01-01
Abstract
A novel synthesis of the renin inhibitor aliskiren based on an unprecedented disconnection between C5 and C6 was developed, in which the CS 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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https://hdl.handle.net/11365/997654
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