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THE ASYMMETRIC HYDROVINYLATION REACTION: APPLICATIONS IN THE SYNTHESIS OF PSEUDOPTEROGORGIA ELISABETHAE NATURAL PRODUCTS

Cox, Glen Adam
http://rave.ohiolink.edu/etdc/view?acc_num=osu1332433731

Abstract Details

2012, Doctor of Philosophy, Ohio State University, Chemistry.
A fundamental challenge in organic synthesis is the stereoselective formation of carbon-carbon bonds. In particular, many difficulties have been encountered in the efficient establishment of exocyclic stereogenic centers, which are a common structural motif in a wide variety of natural products; best exemplified by the diterpenes isolated from marine organism Pseudopterogorgia elisabethae, which contain as many as three exocyclic appendages. The asymmetric hydrovinylation, the heterodimerization of a prochiral olefin with ethylene resulting in the addition of a vinyl group and a hydrogen across a double bond, offers a promising solution to the problem of exocyclic stereochemical control. The power and versatility of the hydrovinylation reaction is demonstrated in the highly enantioselective syntheses of the aglycones of all known pseudopterosins (A-L), displaying unprecedented flexibility for the independent installation of each stereogenic center. In addition, the stereochemical features associated with these syntheses are common to a number of highly bioactive compounds isolated from P. elisabethae, including: serrulatanes, amphilectanes, elisapteranes, colombianes, and elisabethanes. The synthetic efforts, highlighting the use of the hydrovinylation reaction to furnish the desired configuration at each stereogenic center with >95% selectivity are disclosed, offering expeditious entry into this family of biologically important compounds.
T. V. RajanBabu, PhD (Advisor)
Craig Forsyth, PhD (Committee Member)
Jon Parquette, PhD (Committee Member)
295 p.
Chemistry; Organic Chemistry
hydrovinylation; ethylene; enantioselective synthesis; natural product synthesis; terpenes; pseudopterosins; colombiasin A; elisapterosin B; elisabethin A

Recommended Citations

Citations

  • Cox, G. A. (2012). THE ASYMMETRIC HYDROVINYLATION REACTION: APPLICATIONS IN THE SYNTHESIS OF PSEUDOPTEROGORGIA ELISABETHAE NATURAL PRODUCTS [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1332433731

    APA Style (7th edition)

  • Cox, Glen. THE ASYMMETRIC HYDROVINYLATION REACTION: APPLICATIONS IN THE SYNTHESIS OF PSEUDOPTEROGORGIA ELISABETHAE NATURAL PRODUCTS. 2012. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1332433731.

    MLA Style (8th edition)

  • Cox, Glen. "THE ASYMMETRIC HYDROVINYLATION REACTION: APPLICATIONS IN THE SYNTHESIS OF PSEUDOPTEROGORGIA ELISABETHAE NATURAL PRODUCTS." Doctoral dissertation, Ohio State University, 2012. http://rave.ohiolink.edu/etdc/view?acc_num=osu1332433731

    Chicago Manual of Style (17th edition)

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© 2012, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.