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.
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Transannular O-heterocyclization: a useful tool for the total synthesis of Murisolin and 16,19-cis-Murisolin.
Org Lett
November 2012
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, D-48149 Münster, Germany.
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.
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