Date of Graduation

8-2016

Document Type

Dissertation

Degree Name

Doctor of Philosophy in Chemistry (PhD)

Degree Level

Graduate

Department

Chemistry & Biochemistry

Advisor

Matt Mcintosh

Committee Member

Neil Allison

Second Committee Member

Suresh Thallapuranam

Third Committee Member

Wei Shi

Keywords

Pure sciences; Antascomicin B; Asymmetric synthesis; Natural products

Abstract

This dissertation describes studies in the asymmetric synthesis of the C21 – C34 fragment of the natural product, antascomicin B. Antascomicin B is structurally related to FK506, binds strongly to FKBP12, yet does not shown immunosuppressive activity. Small ligand FKBP12 binding complexes were shown to have potent neuroprotective and neuroregenerative properties in mouse models of Parkinson’s disease. The highlighted chemical reactions include an asymmetric transfer hydrogenation (ATH), Ireland-Claisen rearrangement (ICR), directed hydrogenation and allylic diazene rearrangement.

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