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UBC Theses and Dissertations

Efforts towards the total synthesis of nosiheptide Hwang, Hee Jong Jason


This thesis described here aims to achieve the total synthesis of nosiheptide, a representative member of the so-called E-series of thiopeptide antibiotic. Our group has established various techniques for the assembly of their complex molecular framework, and demonstrated the total syntheses of two D-series thiopeptide antibiotics. However, there is no precedent total synthesis of compound belonging to E-series. The part of the reason is that the presence of an additional 3-OH substituent not only adds significant synthetic complications, but also bars the use of the previously established technology. The present work details the assembly of the pyridine-thiazole cluster of E-series thiopeptide substance through a modified Hantzsch reaction that delivers the complete pyridine segment in a triply convergent fashion. Optimization studies related to this pyridine formation have further enhanced the conciseness and simplicity of the method. This chemistry thus developed can be applied to medicinal chemistry investigations in thiopeptide antibiotic field; an endeavor that will possibly unveil valuable new antibiotics.

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Attribution-NonCommercial-NoDerivs 2.5 Canada