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Title:Dearomative reduction of arenes through the use of arenophiles & studies towards the synthesis of cardiotonic steroids calotropin and calactin
Author(s):Nakamata Huynh, Stephanie Mio
Advisor(s):Sarlah, David
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:M.S.
Genre:Thesis
Subject(s):Organic chemistry
Total synthesis
Methodology
Dearomative functionalization
Abstract:A novel method for the dearomative reduction of arenes through the use of N,N-arenophile, MTAD, was developed. Cheap feedstock arenes undergo photocycloaddition with MTAD, and the cycloadduct can be treated further to furnish novel 1,3-cyclohexadienes or 1,4-diamino-2- cyclohexenes. The utility of this method is shown in the synthesis of a natural product in two steps from naphthalene. Calotropin, a cardiotonic steroid, isolated from Apocynaceae plants is a highly cytotoxic natural product with anti-cancer activity. A total synthesis strategy which utilizes a NHC-catalyzed benzoin condensation, and Pd-catalyzed nucleophilic dearomatization of a phenol is described. Also described, is the semisynthetic strategy towards calotropin from estrone, where the aromatic A ring is dearomatized to introduce a C1 fragment at the para-position.
Issue Date:2017-04-27
Type:Text
URI:http://hdl.handle.net/2142/97622
Rights Information:Copyright 2017 Stephanie Nakamata Huynh
Date Available in IDEALS:2017-08-10
Date Deposited:2017-05


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