Dearomative reduction of arenes through the use of arenophiles & studies towards the synthesis of cardiotonic steroids calotropin and calactin
Nakamata Huynh, Stephanie Mio
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https://hdl.handle.net/2142/97622
Description
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
Issue Date
2017-04-27
Director of Research (if dissertation) or Advisor (if thesis)
Sarlah, David
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
M.S.
Degree Level
Thesis
Keyword(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.
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