Authors

Aaron Feldman

Document Type

Restricted

Publication Date

2013

Abstract

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.

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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.

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The views expressed in this paper are solely those of the author.