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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Journal of the Chemical Society, Perkin Transactions 1
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