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.

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