2026-09-21T05:35:40Z https://www.ideals.illinois.edu/oai-pmh

oai:www.ideals.illinois.edu:2142/97622 2023-07-11 col_2142_5131 col_2142_14789 com_2142_5130 com_2142_14788 com_2142_8903

Sarlah, David Nakamata Huynh, Stephanie Mio 2017-08-10T19:52:21Z 2017-08-10T19:52:21Z 2019-08-11T09:15:35Z 2017-04-27 2017-05 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. Submission published under a 24 month embargo labeled 'Closed Access', the embargo will last until 2019-05-01 The student, Stephanie Nakamata Huynh, accepted the attached license on 2017-04-21 at 14:53. The student, Stephanie Nakamata Huynh, submitted this Thesis for approval on 2017-04-21 at 14:58. This Thesis was approved for publication on 2017-04-27 at 17:23. DSpace SAF Submission Ingestion Package generated from Vireo submission #10987 on 2017-08-10 at 14:32:29 Made available in DSpace on 2017-08-10T19:52:21Z (GMT). No. of bitstreams: 2 NAKAMATAHUYNH-THESIS-2017.pdf: 5600857 bytes, checksum: 5e1e6d0e48bace753f59f8cf4dbcde64 (MD5) LICENSE.txt: 4221 bytes, checksum: deaaf9b7a8e7283bbf9c02e1e584317d (MD5) Previous issue date: 2017-04-27 Embargo set by: Colleen Fallaw for item 102675 Lift date: 2019-08-10T21:25:30Z Reason: Author requested closed access (OA after 2yrs) in Vireo ETD system Limited Restriction Lifted for Item 102675 on 2019-08-11T09:15:35Z. application/pdf http://hdl.handle.net/2142/97622 en Copyright 2017 Stephanie Nakamata Huynh Organic chemistry Total synthesis Methodology Dearomative functionalization Dearomative reduction of arenes through the use of arenophiles & studies towards the synthesis of cardiotonic steroids calotropin and calactin text text Chemistry Chemistry University of Illinois at Urbana-Champaign Thesis M.S.