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Issue 22, 2010
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Concise total synthesis and structural revision of (+)-pestalazine B

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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

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Publication details

The article was received on 02 Aug 2010, accepted on 12 Aug 2010 and first published on 17 Sep 2010


Article type: Paper
DOI: 10.1039/C0OB00531B
Citation: Org. Biomol. Chem., 2010,8, 5179-5186
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    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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