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Transannular O‑Heterocyclization: A Useful Tool for the Total Synthesis of Murisolin and 16,19-cis-Murisolin

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journal contribution
posted on 16.11.2012, 00:00 by Peter Persich, Julia Kerschbaumer, Sandra Helling, Barbara Hildmann, Birgit Wibbeling, Günter Haufe
Transannular O-heterocyclization is applied as a key step in a total synthesis. This highly stereoselective and metal-free transformation introduces four stereocenters in one step. It was chosen to be the pivotal step in the synthesis of Murisolin and 16,19-cis-Murisolin, two annonaceous acetogenins. The efficiency of this synthesis is further illustrated by a stereodivergent late-stage separation of both synthetic routes.