Practical Synthesis of a Renin Inhibitor via a Diastereoselective Dieckmann Cyclization
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- 作者：Danny Gauvreau ; Greg J. Hughes ; Stephen Y. W. Lau ; Daniel J. McKay ; Paul D. O’ ; Shea ; Rick R. Sidler ; Bing Yu ; Ian W. Davies
- 刊名：Organic Letters
- 出版年：2010
- 出版时间：November 19, 2010
- 年：2010
- 卷：12
- 期：22
- 页码：5146-5149
- 全文大小：182K
- 年卷期：v.12,no.22(November 19, 2010)
- ISSN：1523-7052
文摘
A scalable synthesis of a potent renin inhibitor (1) is described. The absolute stereochemistry is set via an unprecedented diastereoselective Dieckmann cyclization directed by a remote chiral protecting group. This transformation enables preparation of chiral 1,3-[3.3.1]-diazabicyclononenes by desymmetrization of alkyl-esters, with selectivities ranging from 4 to 17:1.