Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, Lagoas-Marcosende, 36310 Vigo, Spain.
Org Biomol Chem. 2010 Nov 21;8(22):5179-86. doi: 10.1039/c0ob00531b. Epub 2010 Sep 17.
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.
已经通过 4 步反应，以未保护的色氨酸二酮哌嗪与 3a-溴基吡咯啶并吲哚啉的 N-烷基化反应作为关键步骤，实现了（+）-pestalazine B 的目标结构的会聚合成。尽管其结构已通过 X 射线分析得到证实，但光谱数据与天然产物不匹配。该方法的多功能性允许制备几种非对映异构体，生成的数据库提出了天然生物碱的一种异构结构，其中 d-亮氨酸和 d-苯丙氨酸残基交换了位置，这通过全合成得到了证实。
