Date of Award
2017
Degree Type
Dissertation
Degree Name
Doctor of Philosophy (PhD)
Graduate Group
Chemistry
First Advisor
Amos B. Smith
Abstract
The first total syntheses of architecturally complex indole terpenes (−)-nodulisporic acid D and (−)-nodulisporic acid C are reported here via a unified strategy of late-stage union of large fragments. Key synthetic transformations in the total synthesis of (−)-nodulisporic acid D comprise vicinal difunctionalization of an advanced alpha,beta-unsaturated aldehyde to form the trans-fused 5,6-ring system in the eastern hemisphere and a palladium mediated cascade cross-coupling/indolization protocol leading to a multi-substituted indole core. Key synthetic transformations in the total synthesis of (−)-nodulisporic acid C venture include a Nozaki-Hiyama-Kishi reaction leading to a tricyclic western hemisphere intermediate, a late stage tert-butyl carbamate directed ortho-lithiation/prenylation, and a palladium catalyzed cascade cross coupling/indole formation.
Recommended Citation
Zou, Yike, "Synthetic Study Of Structurally Complex Indole Terpenes Total Syntheses Of (─)-Nodulisporic Acid D And (─)-Nodulisporic Acid C In Conjunction With Advanced Synthetic Studies Towards (+)-Nodulisporic Acid A And (─)-Nodulisporic Acid B" (2017). Publicly Accessible Penn Dissertations. 2947.
https://repository.upenn.edu/edissertations/2947