Catalytic asymmetric synthesis of the central tryptophan residue of celogentin C

被引：49

作者：

Castle, SL ^{[1
]}

Srikanth, GSC ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 20期

关键词：

D O I：

10.1021/ol035236x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral phase-transfer catalyst 5 containing an electron-deficient trifluorobenzyl moiety promoted the alkylation of glycine derivative 6 with propargyl bromide 7a in good yield and excellent ee. The resulting propargyl glycine 8 was converted to 14, the central tryptophan residue of Celogentin C, in two steps, with the Pd-catalyzed heteroannulation as the key transformation. This method promises to be an efficient route for the preparation of tryptophan derivatives possessing substitution on the indole ring.

引用

页码：3611 / 3614

页数：4

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