Practical Synthesis of a Renin Inhibitor via a Diastereoselective Dieckmann Cyclization

…, GJ Hughes, SYW Lau, DJ McKay, PD O'Shea…

Index: Gauvreau, Danny; Hughes, Greg J.; Lau, Stephen Y. W.; McKay, Daniel J.; O'Shea, Paul D.; Sidler, Rick R.; Yu, Bing; Davies, Ian W. Organic Letters, 2010 , vol. 12, # 22 p. 5146 - 5149

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Abstract

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.

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