Convergent Synthesis of the Renin Inhibitor Aliskiren Based on C5–C6 Disconnection and CO2H–NH2 Equivalence
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- 作者：Elena Cini ; Luca Banfi ; Giuseppe Barreca ; Luca Carcone ; Luciana Malpezzi ; Fabrizio Manetti ; Giovanni Marras ; Marcello Rasparini ; Renata Riva ; Stephen Roseblade ; Adele Russo ; Maurizio Taddei ; Romina Vitale ; Antonio Zanotti-Gerosa
- 刊名：Organic Process Research & Development
- 出版年：2016
- 出版时间：February 19, 2016
- 年：2016
- 卷：20
- 期：2
- 页码：270-283
- 全文大小：575K
- ISSN：1520-586X
文摘
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.