Solid-phase total synthesis of (-)-Phenylhistine and (-)-Aurantiamine. Synthesis of a diverse dehydro-2,5-diketopiperazine library. Part II

Elias A Couladouros; Alexandros D Magos

doi:10.1007/s11030-005-1295-9

Solid-phase total synthesis of (-)-Phenylhistine and (-)-Aurantiamine. Synthesis of a diverse dehydro-2,5-diketopiperazine library. Part II

Mol Divers. 2005;9(1-3):111-21. doi: 10.1007/s11030-005-1295-9.

Authors

Elias A Couladouros¹, Alexandros D Magos

Affiliation

¹ Chemistry Laboratories, Agricultural University of Athens, Iera Odos 75, Athens 118 55, Greece. ecoula@chem.demokritos.gr

PMID: 15789558
DOI: 10.1007/s11030-005-1295-9

Abstract

The preparation of solid supported glycine phosphonate and its utilization for the total synthesis of two natural products is presented. The proposed protocol combines diversity with accessibility and speed, which makes this scaffold suitable for automated parallel synthesis and combinatorial chemistry. The preparation of a small library of dehydro-2,5-diketopiperazines, combining several natural amino acids with diverse heterocycles (including thiazoles, pyridines, indoles and imidazoles), is also demonstrated.

MeSH terms

Indicators and Reagents
Models, Molecular
Molecular Conformation
Piperazines / chemical synthesis*
Piperazines / chemistry
Spectroscopy, Fourier Transform Infrared

Substances

Indicators and Reagents
Piperazines
aurantiamine