SYNTHESIS OF ASYMMETRICALLY SUBSTITUTED SCYLLO-INOSITOL

Undergraduate Honors Thesis

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Citeable URL: https://scholar.colorado.edu/concern/undergraduate_honors_theses/td96k299d

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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