Issue 0, 1984
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Journal of the Chemical Society, Perkin Transactions 1

Peptidic thiacyclols. Synthesis and structural studies

Giancarlo Zanotti,   Francesco Pinnen,   Gino Lucente,   Silvio Cerrini,   Walter Fedeli  and  Fernando Mazza  

Abstract

Deprotection with tri-n-butylphosphine in aqueous medium of 2-t-butyldithiopropionyl-L-phenylalanyl-L-proline p-nitrophenyl ester gives stable thiacyclols. These compounds are isomeric with nine-membered peptidic thiolactones and possess the same stereochemistry at the phenylalanine and proline chiral centres as found in natural oxacyclols (ergot alkaloids). Spectroscopic properties and an X-ray crystallographic analysis are reported. Crystals of the thiacyclol (14) are orthorhombic with a= 16.462(7), b= 15.763(7), c= 6.487(4)Å, Z= 4, space group P212121.

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Article information

DOI
https://doi.org/10.1039/P19840001153
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 1153-1157

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Peptidic thiacyclols. Synthesis and structural studies

G. Zanotti, F. Pinnen, G. Lucente, S. Cerrini, W. Fedeli and F. Mazza, J. Chem. Soc., Perkin Trans. 1, 1984, 1153 DOI: 10.1039/P19840001153

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