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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.
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Type
research article
Authors
Publication date
2004
Published in
Volume
6
Issue
25
Start page
4707
End page
4710
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
November 22, 2006