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An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (alphaS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine.
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2013 , DOI: 10.3762/bjoc.9.229
Jörg Erdsack 1 , Norbert Krause
Affiliation  

The synthesis of (alphaS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine (22, normethylazafuranomycin) by the gold-catalyzed cycloisomerization of alpha-aminoallene 17 is described. The target molecule was synthesized in 13 linear steps from Cbz-protected Garner aldehyde (R)-2 in an overall yield of 2.4%. The approach was first examined in model studies, which afforded the alkylated azafuranomycin derivative 13a in 2.9% yield over 12 steps.

中文翻译:

通过金催化的丙二烯环异构化制备氮杂呋喃霉素类似物的方法:合成 (alphaS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine。

描述了 (alphaS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine (22, normethylazafuranomycin) 通过金催化的 alpha-aminoallene 17 环异构化的合成。目标分子是由 Cbz 保护的加纳醛 (R)-2 在 13 个线性步骤中合成的,总产率为 2.4%。该方法首先在模型研究中得到检验,该研究通过 12 个步骤以 2.9% 的产率提供烷基化氮杂呋喃霉素衍生物 13a。
更新日期:2017-01-31
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