Synthesis of cyclic peptidomimetics from aldol building blocks.
Aldol products (3-hydroxy acids) with an allyl-protected hydroxy group were converted to amino alcohols by Curtius rearrangement. Combination of the carboxylic acid with the amino alcohols gave the amides 10. Ring-closing metathesis led to the 12-membered lactams 12 as mixtures of E/Z-isomers. The scheme was also transferred to the solid-phase. In this case the macrolactams are formed via cyclorelease. For a pair of E/Z-isomers the solution conformation was determined by ROESY spectroscopy.
Sasmal
Sanjita
S
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany.
Geyer
Armin
A
Maier
Martin E
ME
D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007769:Lactams / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018716:Molecular Mimicry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D000596:Amino Acids; D002264:Carboxylic Acids; D007769:Lactams; D010456:Peptides, Cyclic