- Application of N-Tritylmethionine in the Preparation of Heterocycles of Biological and Synthetic Interest
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Treatment of the methylsulfonium salts of the corresponding N-tritylmethionine derivatives with sodium hydride or potassium tert-butoxide provides the heterocycles N-trityl-L-homoserine lactone (3), (S)- and (R)-3-(N-tritylamino)tetrahydrofuran (7a, 7b), (S)-1-hydroxy-3-(N-tritylamino)-2-pyrrolidinone (14), (S)-4-(N-tritylamino)-1,2-oxazinan-3-one (15), (S)-3-(N-tritylamino)-2-pyrrolidone (23), (S)-1-tert-butyloxycarbonylamino-3-(N-tritylamino)-2-pyrrolidone (27), and (S)-2-methyl-4-(N-tritylamino)-1,2-oxazinan-3-one (18).Methylation of 14 and 15 yields (S)-1-methoxy-3-(N-tritylamino)-2-pyrrolidone (17) and 18, respectively.The stereochemistry of compounds 3, 7a, and 17 has been determined by X-ray crystal structure analysis.
- Barlos, Kleomenis,Papaioannou, Dionysios,Voliotis, Stavros
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p. 1127 - 1134
(2007/10/02)
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- Preparation of Optically Active Cyclic Ether Derivatives of Amino Acids and Peptides
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Treatment of N-tritylmethioninol (1) or peptides (6), incorporating methionyl and amino alcohol residues, with MeI, followed by base mediated cyclisation of the thus derived sulphonium salts, provides the title compounds in excellent yields.
- Barlos, Kleomenis,Papaioannou, Dionysios,Patrianakou, Stella,Sanida, Chariklia,Tsegenidis, Theodoros
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p. 474 - 475
(2007/10/02)
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