Synthesis and properties of allenic natural products and pharmaceuticals.
Nowadays, about 150 natural products comprising an allenic or cumulenic structure are known. The chemistry of these compounds has turned out to be a very attractive and prolific area of interest: advances in the isolation and characterization of new allenic natural products have led to the establishment of efficient synthetic procedures which in many cases also open up an access to enantiomerically pure target molecules. Inspired by the intriguing biological activities of many allenic natural products, allene moieties are now systematically introduced in pharmacologically active classes of compounds (steroids, prostaglandins, amino acids, nucleosides). The functionalized allenes thus obtained often exhibit impressive activities as mechanism-based enzyme inhibitors, cytotoxic, or antiviral agents. A prerequisite for further developments in this field is the efficient stereoselective synthesis of allene derivatives.
ETH Zürich, Laboratorium für Organische Chemie, ETH-Hönggerberg, 8093 Zürich, Switzerland. anja.hoffmann-roeder@carb.org.chem.
Anja
A
Hoffmann-Röder
Norbert
N
Krause
D000466:Alkadienes / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000378:metabolism; D000596:Amino Acids / Q000138:chemical synthesis; D001688:Biological Products / Q000138:chemical synthesis*; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis*; D011453:Prostaglandins / Q000138:chemical synthesis; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis; D013729:Terpenes / Q000138:chemical synthesis / Q000302:isolation & purification
D000466:Alkadienes; D000596:Amino Acids; D001688:Biological Products; D009705:Nucleosides; D004364:Pharmaceutical Preparations; D011453:Prostaglandins; D013256:Steroids; D013729:Terpenes; C025947:propadiene