ORGN 14 |
Ring-opening metathesis/oxy-Cope rearrangement: A new strategy for the synthesis of bicyclic medium ring-containing compounds
| Brian H. White and Marc L. Snapper. Department of Chemistry, Boston College, Merkert Chemistry Center, 2609 Beacon St., Chestnut Hill, MA 02467 |
We have developed a rapid entry into medium sized, carbocyclic rings through an olefin metathesis/oxy-Cope strategy. Ring-closing/ring-opening metathesis of cyclobutenes 1 with Grubbs’ catalyst provides protected cis-divinylcycloalkanols 2. Deprotection and oxy-Cope rearrangement gives the desired medium ring products 3. Insight into the stereochemical outcome of the oxy-Cope rearrangement is gained through additional functionalization of 2 through cross metathesis, and examination of the resulting Cope products. Studies towards the application of this methodology to the synthesis of natural product skeletons will also be discussed. |
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