The practical preparation of eight-membered rings remains a challenging synthetic pursuit. Herein, we have successfully demonstrated the synthesis ofcyclooctanoid systems via a microwave-assisted tandem 6-exo-dig cyclization/Claisen rearrangement on appropriately substituted 5-hexyn-1-ol precursors. The initial base-catalyzed cyclization is facilitated by activation of the triple-bond with an electron-withdrawing substituent. Subsequent Claisen rearrangement of the resulting allyl vinyl ether gives the desired eight-membered ring.
This thesis describes initial optimization and investigates the scope of this novel methodology through the synthesis of a variety of cyclooctanone analogs. Further investigations will include expansion of reaction scope, as well as application of this methodology to natural product synthesis.
Feldman, Aaron, "Facile access to cyclooctanoid systems via microwave-‐assisted sequential 6‐exo‐dig cyclization/Claisen rearrangement" (2013). Chemistry Honors Papers. 11.
The views expressed in this paper are solely those of the author.