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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 …