Improved synthesis of a [4.4]-spirolactam β-turn mimetic as surrogate of the didemnin side chain dipeptide Pro-N-Me-d-Leu |
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Abstract: | An efficient synthesis of 4.4]-spirolactam restricted derivatives of the didemnin side chain dipeptide l-Pro-N-Me-d-Leu is described. This methodology involves: (a) peptide coupling of N-Boc-2-allylproline with d-Leu-OBn; (b) OsO4/NaIO4 mediated allyl oxidation and intramolecular cyclization to the corresponding cyclic hemiaminals; and (c) NaBH4 mediated reduction of an intermediate N-acyliminium ion. This synthetic strategy gave significant better results than the previously reported strategies for the synthesis of 4.4]-spirolactam β-turn mimetics. |
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Keywords: | Didemnins Peptidomimetics β-Turn mimetics Spirolactams Mitsunobu type reaction Hemiaminal reduction |
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