Diastereoselectivity in the solid-phase synthesis of peptide heterocycle hybrids

被引：7
|
作者：
Grimes, JH
Zheng, WF
Kohn, WD
机构：
[1] Eli Lilly & Co, Res Triangle Pk Labs, Res Triangle Pk, NC 27709 USA
[2] Lilly Corp Ctr, Lilly Res Labs, Indianapolis, IN 46285 USA
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 33期
关键词：
2-D NMR; solid-phase synthesis; stereoselective cyclization; peptide-heterocycle;
D O I：
10.1016/j.tetlet.2004.06.075
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sixteen compounds containing the bicyclic moiety (3,8,10-trisubstituted 2,9-dioxo-5-thia-1,8-diazabicyclo[4.4.0]decane) were produced via solid-phase synthesis. Differing substitution at the 3- and 10-positions was used. These were analyzed using 2-D NMR techniques (ROESY) to determine the stereoselectivity of ring formation in the core heterocycle. Conformational analysis of the proposed transition state structure using Sybyl 6.8(R) was used to rationalize the stereochemical outcome of ring formation. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6333 / 6336
页数：4
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