Document Type

Restricted

Advisor

Timo Ovaska

Publication Date

2025

Comments

Access to this paper is restricted to the Connecticut College campus,

Abstract

Guanacastepene A, a tricyclic natural product found in a Costa Rican fungus, poses an interesting synthetic challenge due to its complex ring structure and its promise as a potent antibiotic. The highly functionalized 5-7 bicyclic core of Guanacastepene A has previously been synthesized, but challenges with a key Heck reaction severely limited progress. A new sequence has been designed to efficiently reach an intermediate allylic diol, a key intermediate before cyclization of the seven membered ring of Guanacastepene A.

Next, we hope this synthesis can efficiently be scaled up, allowing for larger production of the cyclization product. This will hopefully allow for functional group interconversions and a ring closing metathesis reaction to form the third, six membered ring of Guanacastepene A. Further functional group manipulations will hopefully complete the synthesis of Guanacastepene A using the Ovaska methodology.

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