Issue 22, 2010

Concise total synthesis and structural revision of (+)-pestalazine B

Abstract

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

Graphical abstract: Concise total synthesis and structural revision of (+)-pestalazine B

Supplementary files

Article information

Article type
Paper
Submitted
02 Aug 2010
Accepted
12 Aug 2010
First published
17 Sep 2010

Org. Biomol. Chem., 2010,8, 5179-5186

Concise total synthesis and structural revision of (+)-pestalazine B

C. Pérez-Balado and Á. R. de Lera, Org. Biomol. Chem., 2010, 8, 5179 DOI: 10.1039/C0OB00531B

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