Concise total synthesis and structural revision of (+)-pestalazine B
Concise total synthesis and structural revision of (+)-pestalazine B
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DOI：
10.1039/c0ob00531b
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发表时间：
2010-01-01
影响因子：
3.2
通讯作者：
de Lera, Angel R.
中科院分区：
文献类型：
--
作者：
Perez-Balado, Carlos;de Lera, Angel R.
采用3 α-溴吡咯烷吲哚啉与未保护的色氨酸二酮哌嗪的N-烷基化反应作为关键步骤，通过4步反应实现了（+）-哌嗪B的收敛合成。虽然它的结构被X射线分析证实，但光谱数据与天然产物的光谱数据不匹配。该方法的多功能性允许制备几种非对映体，并且生成的数据库导致提出天然生物碱的异构体结构，其中D-亮氨酸和D-苯丙氨酸残基交换位置，这被全合成证实
A convergent synthesis of the proposed structure of (+)-pestalazine B has been achieved in 4 steps using the N-alkylation of an unprotected tryptophan diketopiperazine with a 3a-bromopyrrolidinoindoline as the key step. Although its structure was confirmed by X-ray analysis, the spectroscopic data did not match those of the natural product. The versatility of the methodology allowed the preparation of several diastereomers, and the database generated led to the proposal of an isomeric structure for the natural alkaloid where the D-leucine and D-phenylalanine residues exchanged positions, which was corroborated by total synthesis