Synthetic studies on the pluramycin family of antitumor antibiotics : the total synthesis of isokidamycin

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Synthetic studies on the pluramycin family of antitumor antibiotics : the total synthesis of isokidamycin

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Title: Synthetic studies on the pluramycin family of antitumor antibiotics : the total synthesis of isokidamycin
Author: O'Keefe, Brian Michael
Abstract: A total synthesis of the complex C-aryl glycoside isokidamycin was achieved during an effort to construct the natural product kidamycin, a member of the pluramycin family of antitumor antibiotics. The angolosamine carbohydrate was appended, along with annelation of a benzene ring by the implementation of the Martin group's silicon tether-directed, intramolecular aryne-furan cycloaddition strategy. The vancosamine-derived carbohydrate was then installed by an O -> C-glycoside rearrangement. A novel protocol for the carbonylative cross-coupling of ortho-disubstituted aryl iodides with aryl boronic acids and alkynyl zinc reagents was also discovered during efforts to introduce the pyranone ring of kidamycin. The reaction proved general, as a variety of electron-rich and electron-poor aryl iodides, boronic acids, and alkynyl-zinc reagents participated in the cross-coupling.
Department: Chemistry
Subject: Total synthesis Pluramycins Kidamycin Isokidamycin c-aryl glycosides Natural products Carbonylative cross-coupling Cross-coupling Palladium
URI: http://hdl.handle.net/2152/ETD-UT-2010-12-2035
Date: 2010-12

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