Amino acid motifs in natural products: synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine

• Oliver Ries,
• Martin Büschleb,
• Markus Granitzka,
• Dietmar Stalke and
• Christian Ducho

Beilstein J. Org. Chem. 2014, 10, 1135–1142, doi:10.3762/bjoc.10.113

• opening up an excellent approach for the synthesis of bioactive natural products and derivatives thereof for structure activity relationship (SAR) studies. Keywords: chiral pool; cross metathesis; esterification; β-hydroxy-α-amino acids; natural products; Introduction Besides the proteinogenic β-hydroxy

• -Fmoc-protected building blocks potentially suitable for solid-phase peptide synthesis (SPPS). It is well established that O-acylated β-hydroxy-α-amino acids can be used in Fmoc-strategy peptide syntheses without migration of the acyl unit [37][38][39]. Based on these findings, we have desired to

• -α-amino acids serine and threonine, (2S,3S)-3-hydroxyleucine can be found as a substructure of several bioactive natural products. This structural motif often serves as a 'three-way-junction', as for instance in azinothricin [1], citropeptin [2], kettapeptin [3], pipalamycin [4], dentigerumycin [5

N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters

• Takuya Uno,
• Yusuke Kobayashi and
• Yoshiji Takemoto

Beilstein J. Org. Chem. 2012, 8, 1499–1504, doi:10.3762/bjoc.8.169

• synthesis of a variety of heterocyclic compounds [2] and pharmaceutically active products [3][4][5]. In addition, they are valuable intermediates for chiral α-amino acids [6][7], including β-hydroxy-α-amino acids [8][9][10][11][12][13][14]. Consequently, significant efforts have been devoted to synthesizing