Synthesis and Sequestrating Properties of Enterochelin Analogues

Abstract

Acquisition of iron by siderophores is critical for the survival of many microbes. Enterochelin is a catechol siderophore that has a trilactonate macrocylic core derived from serine that is connected to three 2, 3-dihydroxybenzoyl moieties all of which participate in the coordination of an iron atom in a hexadentate fashion. The work described in this thesis is concerned with the development of a viable synthetic pathway to a sulfonamide enterochelin analogue. Starting with L-Serine methyl ester hydrochloride and with the use of 2,2-dibutyl-1,3,2-dioxastannolane a synthetic pathway has been optimised for the synthesis of 3S,7S,11S)-3,7,11-tris(tritylamino)-1,5,9-trioxacyclododecane-2,6,10-trione enabling routine preparation on a multi-gram scale. Improvements have been made to the synthetic pathway towards the synthesis of 2,3-dimethoxybenzenesulfonyl chloride including a one-step conversion of tert-butyl (2,3-dimethoxyphenyl) carbamate to 2,3-dimethoxyanaline hydrochloride using HCl in dioxane.

Date of Award	31 Dec 2019
Original language	English
Awarding Institution	The University of Manchester
Supervisor	Peter Quayle (Supervisor) & Roger Whitehead (Supervisor)