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Synthesis, Characterization, and Applications of Chiral Amino Acid Derived Pyrrolines

Jackson, Daniel Paul
http://rave.ohiolink.edu/etdc/view?acc_num=akron1430819653

Abstract Details

2015, Doctor of Philosophy, University of Akron, Chemistry.
ABSTRACT Many alkaloids, those usually containing a pyrroldiine ring, exist in many natural products and are often used in organocatalysis. Synthetic chemists have thus taken advantage of various pyrroline intermediates in order to achieve target molecules. This dissertation will describe a logical approach to the syntheses of tropane alkaloid analogues and polyhydroxylated pyrrolidines. The latter poises an interesting model for developing chiral auxiliaries for enantioselective reactions. Chapter I of this work provides a brief overview into the pyrrolidine alkaloids and explains the significance of various pyrroline intermediates. The 3-pyrroline system is appealing because the placement of the p-bond allows for further functionilzation to a meso pyrrolidine diol, which will be useful in catalysis later. Chapter II then describes the progression of organocatalysis with a focus on carbon-carbon bonding forming reactions with allylsilanes and carbonyl reductions with boranes. The former reaction is a modification of the Hosomi-Sakurai reaction and utilizes the alkaloids derived in chapter I to make silacycles, where coordination of the electrophile causes a conformational change to allow selective allylation to occur. The latter reaction also utilizes the previous alkaloids to generate the corresponding boracyle to transfer a hydride towards electrophiles. Chapter III highlights the attempts of utilizting amino acid derived 3-pyrroline intermediates towards the syntheses of several natural product analogues. A foundation was laid for these target molecules, which would then be further investigated for biological activity and potentially serve as useful chiral auxiliaries in asymmetric synthesis.
Michael Taschner, Dr. (Advisor)
Claire Tessier, Dr. (Committee Member)
Wiley Youngs, Dr. (Committee Member)
David Modarelli, Dr. (Committee Member)
Bi-min Zhang Newby, Dr. (Committee Member)
152 p.
Chemistry
amino acids; pyrrolines; pyrrolidines; organocatalyst; tropane alkaloids; azasugars

Recommended Citations

Citations

  • Jackson, D. P. (2015). Synthesis, Characterization, and Applications of Chiral Amino Acid Derived Pyrrolines [Doctoral dissertation, University of Akron]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=akron1430819653

    APA Style (7th edition)

  • Jackson, Daniel. Synthesis, Characterization, and Applications of Chiral Amino Acid Derived Pyrrolines. 2015. University of Akron, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=akron1430819653.

    MLA Style (8th edition)

  • Jackson, Daniel. "Synthesis, Characterization, and Applications of Chiral Amino Acid Derived Pyrrolines." Doctoral dissertation, University of Akron, 2015. http://rave.ohiolink.edu/etdc/view?acc_num=akron1430819653

    Chicago Manual of Style (17th edition)

akron1430819653
2,002
© 2015, all rights reserved.
This open access ETD is published by University of Akron and OhioLINK.