UC Santa Barbara

In the Zakarian group, we are interested in the synthesis and application of marine natural products. Elucidating the biological properties of marine natural products is often hampered by a lack of its availability from natural sources in meaningful quantities. Therefore, chemical synthesis remains the most viable option for the production of these molecules. The syntheses of marine natural products frequently open opportunities to develop new synthetic methods, which push the boundaries of current state-of-the-art bond constructions.

Herein, we report the total synthesis and structural revision of (+)-muironolide A. Asymmetric intramolecular Diels-Alder reaction and late stage macrolactonization were the key transformations used for the synthesis of muironolide A, which led us to the reassignment of its structure as (−)-C21-epi-muironolide A.

The second portion describes the late stage derivatization of pinnatoxin compounds. The ultimate goal for pinnatoxin derivatives is introducing 18F, 13C and 3H isotope labeling to probe cellular metabolism and biodistribution in biological systems. This work builds upon a growing body of information that will provide an understanding of the full biological profile of the structurally complex pinnatoxin compounds.

The last portion of this thesis will focus on synthetic studies towards the synthesis of pteriatoxin A. A regioselective catalytic asymmetric dihydroxylation of pinnatoxin G is the featured method for the installment of the 1,2-diol moiety. Establishing this key step could secure a concise route for the total synthesis of pteriatoxin A.