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Studies towards the asymmetric total synthesis of oximidines I and II

Oppenheimer, Jossian
http://rave.ohiolink.edu/etdc/view?acc_num=osu1111764752

Abstract Details

2005, Doctor of Philosophy, Ohio State University, Chemistry.
The oximidines are characterized by a benzo-fused macrolactone bearing an N-acylated enamine side chain, and are among a family of natural products known as benzolactone enamides. Nearly all the members of this family exhibit potent antitumor activity. One particular family, the oximidines, showed selective inhibition of mammalian vacuolar-type proton ATPase. In this thesis, a regio- and stereoselective approach to the macrolactone ring system of the oximidines is described. This approach is based on the ring-closing metathesis as a key reaction. The successful application of this reaction in the present context provided an exceptionally efficient and direct entry into the structurally and biologically interesting class of cytotoxic natural product. Based on this strategy, a regio- and stereoselective synthesis of the fully functionalized oximidine I core structure was achieved. Efforts towards the asymmetric total synthesis of oximidine I and II will be described.
Robert Coleman (Advisor)
202 p.
Chemistry, Organic
1H; Hz; OXIMIDINES; ArH; RCM; TBSO

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Citations

  • Oppenheimer, J. (2005). Studies towards the asymmetric total synthesis of oximidines I and II [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1111764752

    APA Style (7th edition)

  • Oppenheimer, Jossian. Studies towards the asymmetric total synthesis of oximidines I and II. 2005. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1111764752.

    MLA Style (8th edition)

  • Oppenheimer, Jossian. "Studies towards the asymmetric total synthesis of oximidines I and II." Doctoral dissertation, Ohio State University, 2005. http://rave.ohiolink.edu/etdc/view?acc_num=osu1111764752

    Chicago Manual of Style (17th edition)

osu1111764752
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© 2005, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.