Tetrahedron Letters

A formal synthesis of (+)-lactacystin from 4-hydroxyproline

DK Mycock, PA Glossop, W Lewis, CJ Hayes

文献索引：Mycock, David K.; Glossop, Paul A.; Lewis, William; Hayes, Christopher J. Tetrahedron Letters, 2013 , vol. 54, # 1 p. 55 - 57

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被引用次数: 5

摘要

A formal synthesis of (+)-lactacystin has been completed from trans-4-hydroxyproline, using a diastereoselective enolate acylation reaction as a key step. Diastereoselectivity was seen to vary as a function of the steric bulk of the C4-O-protecting group, and contrary to expectations, the best diastereoselectivities were obtained when the small methyl carbonate protecting group was used. The formal synthesis was then completed by intercepting ...