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Progress Towards The Total Synthesis Of Amphidinolide C, Nicholas A. Morra
Progress Towards The Total Synthesis Of Amphidinolide C, Nicholas A. Morra
Electronic Thesis and Dissertation Repository
A second generation catalyst for the Mukaiyama oxidative cyclization for the formation of trans-THF rings is described. Co(nmp)2, displays increased stability to the reaction conditions, resulting in lower catalyst loadings, lower reaction temperatures, and significantly higher purity and yields of the products. Three procedures have been developed with this new water-soluble catalyst that greatly simplifies the post-reaction purification, making this procedure the premier method of forming trans-THF rings.
This new catalyst has been applied towards the total synthesis of the potently bioactive macrocycle, Amphidinolide C. Herein we report the successful synthesis of several fragments of the …
Synthesis Of (±)-Quebrachamine, Tetrahydroisoquinocarbazoles, And Progress Towards Biselide A And E, Barbora Morra
Synthesis Of (±)-Quebrachamine, Tetrahydroisoquinocarbazoles, And Progress Towards Biselide A And E, Barbora Morra
Electronic Thesis and Dissertation Repository
A variety of methodologies developed in our research group have inspired the three separate projects reported. First, the total synthesis of (±)-quebrachamine was performed in 13 steps and 17.8% overall yield. Highlights of the synthesis include an efficient preparation of a functionalized indole core via a [3+2] annulation cycloaddition reaction between a functionalized nitrile and donor-acceptor cyclopropane and a photo induced 9-membered ring closure.
Secondly, we have reported the most efficent and highest yielding route to several tetrahydroisoquinocarbazoles, where the core was prepared in six steps from tryptophol in 51% overall yield. This work highlights for the first time the …