Traditional cyclization methods are often ineffective when attempting to create cyclooctanoids, however there are many biologically active natural products with 8-membered rings that warrant interest. A methodology developed in the Ovaska lab has been shown to produce 8-membered ring systems in good yield from properly substituted 5-alkyn-1-ols. This method takes advantage of the steric effects produced by a geminal dimethyl moiety along a carbon chain to encourage cyclization. Use of this technique to create 8-membered heterocycles containing a nitrogen in place of the geminal dimethyl moiety is currently being explored and will be presented.

Synthesis of a nitrogen containing cyclooctanoid structure via tandem 6-exo dig cyclization/Claisen Rearrangement

255th National Meeting (2018)

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