Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue -, Pages 1135-1142Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.10.113
Keywords
chiral pool; cross metathesis; esterification; beta-hydroxy-alpha-amino acids; natural products
Categories
Funding
- Deutsche Forschungsgemeinschaft (DFG) [SFB 803]
- Fonds der Chemischen Industrie (FCI, Sachkostenzuschuss)
- Danish National Research Foundation (DNRF)
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(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.
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