title: Amino acid motifs in natural products: synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine.
abstract: (2S,3S)-3-Hydroxyleucine can be found in an increasing number of bioactive natural products. Within the context of our work regarding the total synthesis of muraymycin nucleoside antibiotics, we have developed a synthetic approach towards (2S,3S)-3-hydroxyleucine building blocks. Application of different protecting group patterns led to building blocks suitable for C- or N-terminal derivatization as well as for solid-phase peptide synthesis. With respect to according motifs occurring in natural products, we have converted these building blocks into 3-O-acylated structures. Utilizing an esterification and cross-metathesis protocol, (2S,3S)-3-hydroxyleucine derivatives were synthesized, thus opening up an excellent approach for the synthesis of bioactive natural products and derivatives thereof for structure activity relationship (SAR) studies.
authors.affiliation: Department of Chemistry, Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstr. 2, 37077 Göttingen, Germany.
authors.forename: Oliver
authors.initials: O
authors.lastname: Ries
authors.affiliation: Department of Chemistry, Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstr. 2, 37077 Göttingen, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Büschleb
authors.affiliation: Department of Chemistry, Institute of Inorganic Chemistry, Georg-August-University Göttingen, Tammannstr. 4, 37077 Göttingen, Germany.
authors.forename: Markus
authors.initials: M
authors.lastname: Granitzka
authors.affiliation: Department of Chemistry, Institute of Inorganic Chemistry, Georg-August-University Göttingen, Tammannstr. 4, 37077 Göttingen, Germany.
authors.forename: Dietmar
authors.initials: D
authors.lastname: Stalke
authors.affiliation: Department of Chemistry, Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstr. 2, 37077 Göttingen, Germany ; Department of Pharmacy, Pharmaceutical and Medicinal Chemistry, Saarland University, Campus C2 3, 66123 Saarbrücken, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Ducho
keywords: chiral pool; cross metathesis; esterification; natural products; β-hydroxy-α-amino acids