Synthesis of the pro-gly dipeptide alkene isostere using olefin cross-metathesis.
Synthesis of the pro-gly dipeptide alkene isostere using olefin cross-metathesis.
复制标题
使用烯烃交叉复分解合成前甘氨酸二肽烯烃等排体。
DOI：
10.1002/chin.200304184
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发表时间：
2002
期刊：
影响因子：
--
通讯作者：
Scott J. Miller
中科院分区：
文献类型：
--
作者：
M. Vasbinder;Scott J. Miller
提出了一种利用分子间烯烃交叉复分解合成二肽烯烃电子等排体的方法。特别是，报道了 Pro-Gly 电子等排体 (1) 的合成。将 N-BOC-脯氨酸转化为相应的乙烯基取代的氨基甲酸酯，提供 N 端交叉复分解配偶体 (2)。 3-丁烯酸甲酯(3)用作C端组分。以优化的摩尔比处理这两种组分，得到叉产物 1（83% 产率）。还演示了另外三个示例来评估该方法的潜力。
An approach to the synthesis of dipeptide olefin isosteres using intermolecular olefin cross-metathesis is presented. In particular, a synthesis of the Pro-Gly isostere (1) is reported. Conversion of N-BOC-proline into the corresponding vinyl-substituted carbamate provides the N-terminal cross-metathesis partner (2). Methyl 3-butenoate (3) is employed as the C-terminal component. Treatment of the two partners in an optimized molar ratio affords the cross product 1 (83% yield). Three other examples are demonstrated to evaluate the potential of the approach.