Abstract

The goal of our research is to prepare natural products and related core structures through oxidative dearomatization. The development of a stereoselective iron (III)-mediated intramolecular cascade dearomatization of phenol allowed access to various spirocyclohexadienones and tropons in one step using potassium ferricyanide via single electron transfer (SET). Using this oxidative dearomatization reaction, the thesis focuses on three main parts. The first part is the synthetic efforts toward total synthesis of Harringtonolide. The second part focused on the synthesis of spiro[4.5]decane, a core structure in multiple natural products. The spiro compounds were prepared from ortho hydroxyphenyl nitroalkanes using SET reaction with good yield and diastereoselectivity. In the third part, we worked towards the total synthesis of both Magellanine and Megalleninone by applying this novel methodology. The fourth part was the first total synthesis of Phaeocauliine D and L which were achieved from commercially available methyl-4-methyl salicylate in 9-13 simple steps.

Graduation Date

2020

Semester

Fall

Advisor

Yuan, Yu

Degree

Doctor of Philosophy (Ph.D.)

College

College of Sciences

Department

Chemistry

Degree Program

Chemistry

Format

application/pdf

Identifier

CFE0008322

Language

English

Release Date

December 2020

Length of Campus-only Access

None

Access Status

Doctoral Dissertation (Open Access)

Included in

Chemistry Commons

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