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COPPER(I) CATALYZED EXO-SELECTIVE [CN+C+CC] 1,3-DIPOLAR CYCLOADDITIONS and STUDIES TOWARDS THE TOTAL SYNTHESIS OF KAITOCEPHALIN

HU, JIEYU
http://rave.ohiolink.edu/etdc/view?acc_num=case1269965489

Abstract Details

2010, Doctor of Philosophy, Case Western Reserve University, Chemistry.
A novel exo-selective [CN+C+CC] 1,3-dipolar cycloaddition catalyzed by Cu(I)-phosphine ligand complex has been developed for ring formation using a chiral glycyl sultam exerting powerful stereochemical control with an aldehyde and an activated olefin. It is the best exo-selective condition so far reported that is suitable for use with a variety of aliphatic aldehydes. This method has great potential in natural product synthesis for the construction of tri- or tetra-substituted pyrrolidine rings bearing an α- aliphatic chain. A new synthetic route to kaitocephalin, a glutamate receptor antagonist, has been designed featuring a disubstituted pyrrolidine as the key intermediate. An auxiliarycontrolled [CN+C+CC] 1,3-dipolar cycloaddition followed by removal of auxiliary and sulfone was employed to synthesize 2,5-disubstituted pyrrolidines. The key intermediate disubstituted pyrrolidine was prepared in 10 steps and 4% overall yield. Acylation at C4 introduced the C1-C3 moiety and afforded an important precursor to kaitocephalin bearing a complete carbon skeleton in 8% unoptimized yield.
Anthony J. Pearson, PhD (Advisor)
John Protasiewicz, PhD (Committee Chair)
Gregory Tochtrop, PhD (Committee Member)
Geneviève Sauvé, PhD (Committee Member)
Yanming Wang, PhD (Committee Member)
338 p.
Organic Chemistry
[CN+C+CC] 1; 3-dipolar cycloaddition auxiliary Kaitocephalin exo-selective

Recommended Citations

Citations

  • HU, J. (2010). COPPER(I) CATALYZED EXO-SELECTIVE [CN+C+CC] 1,3-DIPOLAR CYCLOADDITIONS and STUDIES TOWARDS THE TOTAL SYNTHESIS OF KAITOCEPHALIN [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1269965489

    APA Style (7th edition)

  • HU, JIEYU. COPPER(I) CATALYZED EXO-SELECTIVE [CN+C+CC] 1,3-DIPOLAR CYCLOADDITIONS and STUDIES TOWARDS THE TOTAL SYNTHESIS OF KAITOCEPHALIN. 2010. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1269965489.

    MLA Style (8th edition)

  • HU, JIEYU. "COPPER(I) CATALYZED EXO-SELECTIVE [CN+C+CC] 1,3-DIPOLAR CYCLOADDITIONS and STUDIES TOWARDS THE TOTAL SYNTHESIS OF KAITOCEPHALIN." Doctoral dissertation, Case Western Reserve University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=case1269965489

    Chicago Manual of Style (17th edition)

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© 2010, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.