Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates

被引:40
作者
Nielsen, TE [1 ]
Le Quement, S [1 ]
Meldal, M [1 ]
机构
[1] SPOCC Ctr, Carlsberg Lab, DK-2500 Copenhagen, Denmark
关键词
D O I
10.1021/ol050871j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHCS] A general strategy for the solid-phase synthesis of structurally diverse bicyclic dipeptide mimetics is presented. Depending on the amino acid side-chain (R-1), peptide-derived N-acyliminium intermediates may undergo nucleophilic attack from either side-chain functional groups (-OH, -NH2, -SH, and -CONH2) or the amide backbone (-CONH-) of the peptide, thus affording a range of aza-, thia-, and oxabicycloalkanes in excellent purity and diastereoselectivity.
引用
收藏
页码:3601 / 3604
页数:4
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