Tetrahedron letters

Synthetic studies on maduropeptin chromophore 2. Synthesis of the madurosamine aryl amide and the C1′ C9′ fragments

KC Nicolaou, K Koide, J Xu, MH Izraelewicz

Index: Nicolaou; Koide, Kazunori; Xu, Jinyou; Izraelewicz, Mark H. Tetrahedron Letters, 1997 , vol. 38, # 21 p. 3671 - 3674

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Citation Number: 11

Abstract

A retrosynthetic analysis (Scheme 1) of maduropeptin chromophore artifact 1 defined compounds 2 and 3 as required building blocks. The construction of 2 was achieved starting from the 2, 5-dimethyl derived aromatic acid 8 and the d-serine derived δ-lactone 12 (Scheme 2), whereas the synthesis of 3 utilized an Evans's aldol condensation reaction between aldehyde 13 and chiral auxiliary 14 (Scheme 3).