Tetrahedron

Improved synthesis of a [4.4]-spirolactam β-turn mimetic as surrogate of the didemnin side chain dipeptide Pro-N-Me-d-Leu

M Gutiérrez-Rodrıguez, MT Garcıa-López, R Herranz

文献索引：Gutierrez-Rodriguez, Marta; Garcia-Lopez, M. Teresa; Herranz, Rosario Tetrahedron, 2004 , vol. 60, # 24 p. 5177 - 5183

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被引用次数: 17

摘要

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 ...