Practical Synthesis of a Renin Inhibitor via a Diastereoselective Dieckmann Cyclization
…, GJ Hughes, SYW Lau, DJ McKay, PD O'Shea…
文献索引：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
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.
[Ace, Karl W.; Armitage, Mark A.; Bellingham, Richard K.; Blackler, Paul D.; Ennis, David S.; Hussain, Nigel; Lathbury, David C.; Morgan, David O.; O'Connor, Noah; Oakes, Graham H.; Passey, Stephen C.; Powling, Laurence C. Organic Process Research and Development, 2001 , vol. 5, # 5 p. 479 - 490]
