Triphosgene as highly efficient reagent for the solid-phase coupling of N-alkylated amino acids -: total synthesis of cyclosporin O

被引：51
|
作者：
Thern, B
Rudolph, J
Jung, G [1 ]
机构：
[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
[2] Bayer Corp, Dept Chem, Div Pharmaceut, West Haven, CT 06516 USA
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 28期
关键词：
solid-phase peptide synthesis; triphosgene; N '-methyl amino acids; cyclosporin;
D O I：
10.1016/S0040-4039(02)00657-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel, highly efficient and racemization free coupling procedure for sterically hindered N-alkyl amino acids has been developed using triphosgene and a combination of diisopropylethyl amine (DIEA) and collidine at room temperature. Its efficiency was demonstrated by comparison with other coupling methods for N-alkylated amino acids and by solid-phase synthesis of the immunosuppressant cyclosporin which was obtained in excellent purity and yield. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5013 / 5016
页数：4
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