Synthesis of cyclic peptidosulfonamides by ring-closing metathesis

被引:36
作者
Brouwer, AJ [1 ]
Liskamp, RMJ [1 ]
机构
[1] Univ Utrecht, Utrecht Inst Pharmaceut Sci, Dept Med Chem, NL-3508 TB Utrecht, Netherlands
关键词
D O I
10.1021/jo0358325
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Protected beta-aminoethanesulfonyl chlorides (2a-e) were used in the preparation of sulfonamides 4, 8, 11a-c, and 15. Ring-closing metathesis of sulfonamides 4 and 8 did not lead to the expected nine-membered cyclic peptidosulfonamides. In contrast, the allylated peptidosulfonamides 11a-c and 15 turned out to be suitable precursor systems for ring-closing metathesis using second-generation Grubbs catalyst and nine-membered cyclic peptidosulfonamides were obtained in 47-60% yields. The possibility for incorporation of these cyclic peptidosulfonamides into a peptide sequence was illustrated by the incorporation of an amino acid on the "S"- or "N"-terminus leading to 16 and 18-20, respectively. A model of cyclic peptidosulfonamide 16 hints at an extended-like structure.
引用
收藏
页码:3662 / 3668
页数:7
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