Undergraduate Honors Theses

Thesis Defended

Spring 2018

Document Type

Thesis

Type of Thesis

Departmental Honors

Department

Chemistry

First Advisor

Maciej Walczak

Second Advisor

Robert Parson

Third Advisor

Bradley Olwin

Abstract

This work describes the total synthesis and characterization of an asymmetrically substituted scyllo-inositol. Starting from a cheap an abundant α-D-methylglucoside, generation of the product was achieved in nine steps. This synthesis capitalized on a Ferrier II reaction which generated the inositol core, followed by a selective reduction, protection, and stereochemical inversion to convert the initial myo-inositol to the desired scyllo-inositol. This asymmetric scyllo-inositol will be used in the future as the head of axinelloside A.

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