Many biologically active natural and synthetic compounds incorporate cycloctanoid structures, highlighting the significance of novel strategies for the construction of 8-membered rings. Devising efficient routes for the stereoselective synthesis of cyclooctanoids has been challenging due to unfavorable entropic and enthalpic factors typically associated with traditional annulation strategies. However, the Ovaska lab has developed a facile, microwave-assisted tandem 6-exo dig cyclization/Claisen rearrangement sequence that can access a variety of 8-membered ring systems from appropriately substituted 5-alkyn-1-ols bearing an electron withdrawing group, preferably a cyano group, at the triple bond terminus. This thesis discusses adaptations made to this novel methodology utilizing the Thorpe Ingold effect to access a wider range of cyclooctanoid ring systems. Additionally, the Baylis-Hillman reaction and synthetic routes to access heterocyclic octanoids were pursued.
Stone, Elizabeth, "Novel Synthesis of Cyclooctanoid Ring Systems Via Tandem 6-exo Dig Cyclization/Claisen Rearrangement Sequence" (2016). Chemistry Honors Papers. 18.
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