A series of novel optically pure aminoindolizidines featuring fused tetrahydro‐furan, thiophene, or pyrrole ring were synthesized from the proteinogenic L‐glutamic acid as a chiral precursor and a nitrogen atom source. The synthetic sequence employed tricyclic indolizidinols as advanced building blocks, which were prepared on a gram‐scale from bioavailable reagents. Key transformations within the used synthetic sequence included diastereoselective Thompson azidation, Staudinger reduction, Jurjew reaction, and highly diastereoselective catalytic hydrogenation. These steps facilitated the efficient and stereoselective synthesis of the ultimate amino‐ and N‐acetylamino‐indolizidines.

中文翻译：

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以 L-谷氨酸为起点，用熔融呋喃、噻吩和吡咯环的非对映选择性进入新型氨基吲哚嗪


以蛋白原性 L-谷氨酸为手性前体和氮原子源，合成了一系列具有熔融四氢呋喃、噻吩或吡咯环的新型光学纯氨基吲哚嗪。合成序列采用三环吲哚嗪二醇作为高级构建单元，其由生物可利用试剂在克级制备。所用合成序列中的关键转化包括非对映选择性 Thompson 叠氮化、Staudinger 还原、Jurjew 反应和高度非对映选择性催化氢化。这些步骤促进了最终氨基和 N-乙酰氨基-吲哚嗪的高效和立体选择性合成。