Synthesis of 11-deoxyanthracyclines

dc.contributor.advisor George A. Kraus
dc.contributor.author Woo, Soon Hyung
dc.contributor.department Chemistry
dc.date 2018-08-15T06:00:49.000
dc.date.accessioned 2020-07-02T06:12:43Z
dc.date.available 2020-07-02T06:12:43Z
dc.date.copyright Thu Jan 01 00:00:00 UTC 1987
dc.date.issued 1987
dc.description.abstract <p>The total synthesis of anthracycline antibiotics is believed to be among the most promising subjects for the development of new drugs for the treatment of human cancers. It was the purpose of this research to develop novel synthetic approaches to 11-deoxyanthracyclines;Part I describes the successful total synthesis of 11-deoxydaunomycinone and 4-demethoxy 11-deoxydaunomycinone by a sequence involving an acyl transfer reaction followed by a tandem Claisen-Diels-Alder reaction. Oxidation of the resulting [beta]-diketone with DDQ provides the tricyclic naphthoquinone which contains functionality well suited for the synthesis of 11-deoxyanthracyclines with different D ring substitution. Subsequent Diels-Alder reaction with either 1-methoxy-1,3-cyclohexadiene or 1-trimethylsilyloxy-1,3-butadiene produces adducts which can be transformed into 11-deoxydaunomycinone and its 4-demethoxy analogue;Part II describes the direct and operationally convenient synthesis of linear polycyclic quinones via the Diels-Alder reaction of quinone sulfoxides. The mild conditions required to effect both Diels-Alder reaction and elimination of phenylsulfinic acid represent a useful feature of this reaction. The utility of this method is demonstrated further by the regiospecific preparation of the tricyclic quinone sulfoxide and its use for the construction of the tetracyclic framework of the 11-deoxyanthracycline nucleus.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/rtd/9319/
dc.identifier.articleid 10318
dc.identifier.contextkey 6355966
dc.identifier.doi https://doi.org/10.31274/rtd-180813-11112
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath rtd/9319
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/82405
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/rtd/9319/r_8805154.pdf|||Sat Jan 15 02:31:35 UTC 2022
dc.subject.disciplines Organic Chemistry
dc.subject.keywords Chemistry
dc.subject.keywords Chemistry
dc.subject.keywords Organic
dc.title Synthesis of 11-deoxyanthracyclines
dc.type article
dc.type.genre dissertation
dspace.entity.type Publication
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
thesis.degree.level dissertation
thesis.degree.name Doctor of Philosophy
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