Total synthesis of anachelin H.
[structure: see text] The first total synthesis of anachelin H is reported. Starting from L-Ser, a stereodivergent synthesis of the polyketide fragment resulting in all possible diastereoisomers is described. The alkaloid peptide fragment is prepared via a tellurium-mediated oxidative aza annulation as the key step. Coupling of the fragments gave synthetic anachelin H, which was found to be identical to a sample of the natural product, thus confirming the configuration by total synthesis.
Gademann
Karl
K
Laboratorium für Organische Chemie der ETH Zürich, CH-8093 Zürich. gademann@org.chem.ethz.ch
Bethuel
Yann
Y
D002851:Chromatography, High Pressure Liquid; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry; D011806:Quinolinium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012694:Serine / Q000737:chemistry; D013237:Stereoisomerism
D009842:Oligopeptides; D010446:Peptide Fragments; D011806:Quinolinium Compounds; C420972:anachelin; D012694:Serine