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

页码：5013 / 5016

页数：4

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