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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A concise, stereocontrolled total synthesis of rippertenol
Scott A Snyder1, Daniel A Wespe, J Marian von Hof
1Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, USA. sas2197@columbia.edu
Abstract:
The first total synthesis of the unique terpene rippertenol, a molecule with dense stereochemical complexity arrayed on a compact framework largely devoid of functional groups, is described. Key elements include orchestrated and unique applications of aldol condensations, Diels-Alder chemistry, and a ring expansion to advance a chiral starting material containing a single chiral center into the final target in a concise and diastereocontrolled manner.
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