Date of Award

Fall 2011

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Graduate Group

Chemistry

First Advisor

Amos B. Smith, III

Abstract

(+)-Nodulisporic Acid A (NsAA) is an indole diterpene of complex structure, isolated from the fungus nodulisporium sp., possessing potent insecticidal activity. Herein is described a new tactic for the construction of complex indoles employing a tandem palladium-mediated process between a haloindoline and a vinyl bromide or triflate.

Chapter 1 of this work will review the efforts by Merck and Co. that lead to the isolation and discovery of potent analogs of NsAA, as well as briefly review the history of complex indole synthesis in the Smith Research Group.

Chapter 2 will describe efforts to streamline the synthesis of the chiral, non-racemic material used to make different variants of the eastern hemisphere sub-target, the development of a new tactic for bringing the two hemispheres together, and efforts to synthesize an eastern hemisphere sub-target that contains the sidechain of NsAA.

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