A total synthesis of hydroxylysine in protected form and investigations of the reductive opening of p-methoxybenzylidene acetals

T Gustafsson, M Schou, F Almqvist…

文献索引：Gustafsson, Tomas; Schou, Magnus; Almqvist, Fredrik; Kihlberg, Jan Journal of Organic Chemistry, 2004 , vol. 69, # 25 p. 8694 - 8701

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被引用次数: 23

摘要

A synthesis of (2 S, 5 R)-5-hydoxylysine, based on (R)-malic acid and Williams glycine template as chiral precursors, has been developed. This afforded hydroxylysine, suitably protected for direct use in peptide synthesis, in 32% yield over the 13-step sequence. Regioselective reductive opening of ap-methoxybenzylidene acetal and alkylation of the Williams glycine template were key steps in the synthetic sequence. Surprisingly, the ...