1. Concise total synthesis and structural revision of (+)-pestalazine B.
- Author
-
Pérez-Balado C and de Lera AR
- Subjects
- Alkylation, Indicators and Reagents, Indoles chemistry, Magnetic Resonance Spectroscopy, Molecular Conformation, Stereoisomerism, Tryptophan chemistry, Alkaloids chemical synthesis, Alkaloids chemistry, Chemistry, Organic methods, Diketopiperazines chemical synthesis, Diketopiperazines chemistry, Indole Alkaloids chemical synthesis, Indole Alkaloids chemistry
- 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.
- Published
- 2010
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