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Access Type

WSU Access

Date of Award

January 2017

Degree Type


Degree Name




First Advisor

Jennifer L. Stockdill


The Daphniphyllum alkaloids are polycyclic natural products isolated from evergreen trees and shrubs native to areas of Southeast Asia. Their structural complexity and biological activity has motived the synthetic community to devise unique strategies to access these molecules. An elegant biomimetic synthesis of methyl homodaphniphyllate by Heathcock and co-workers in 1992 was the first reported total synthesis of a Daphniphyllum alkaloid. In the years since that report, approximately 300 Daphniphyllum alkaloids have been isolated and reported. This recent flood of discovery has been met with an analogous upsurge of interest. Since 2011, 10 total syntheses and several partial syntheses of Daphniphyllum alkaloids have been reported.

In our retrosynthetic analysis of calyciphylline A and daphnicyclidin-type alkaloids, we imagined that a N-centered radical tandem cyclization would rapidly build their tricyclic. Indeed, this key cyclization was achieved and we were compelled to pursue the total synthesis of the target molecules.

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