2026-09-20T16:01:44Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/1096762026-06-16T18:53:34Zcom_1721.1_7582com_1721.1_7581col_1721.1_131022
Timothy F. Jamison.
Kelley, Elizabeth H. (Elizabeth Helen)
Massachusetts Institute of Technology. Department of Chemistry.
Massachusetts Institute of Technology. Department of Chemistry
2017-06-06T19:24:50Z
2017-06-06T19:24:50Z
2017
2017
http://hdl.handle.net/1721.1/109676
988609284
Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2017.
Cataloged from PDF version of thesis.
Includes bibliographical references.
Progress toward the total syntheses of tamulamides A and B, two of the more recently isolated members of the marine ladder polyether family of natural products, is described. The tricyclic cores of the both the ABC fragment and the EFG fragment have been achieved. The fused tetrahydrofuran triad core of the ABC fragment has been synthesized via a base-mediated diepoxide cascade. The challenging 6,7,6 framework of the EFG fragment has been achieved through an intramolecular reductive cyclization reaction. With successful routes to the ABC and EFG cores in hand, current work is focused on elaboration of these intermediates to the desired Wittig coupling partners en route to the first total syntheses of tamulamides A and B ... [diagrams].
by Elizabeth H. Kelley.
Ph.D.
205 pages
eng
Massachusetts Institute of Technology
MIT theses are protected by copyright. They may be viewed, downloaded, or printed from this source but further reproduction or distribution in any format is prohibited without written permission.
http://dspace.mit.edu/handle/1721.1/7582
Chemistry.
Studies toward the total syntheses of tamulamides A and B
Thesis
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<Abstract>Progress toward the total syntheses of tamulamides A and B, two of the more recently isolated members of the marine ladder polyether family of natural products, is described. The tricyclic cores of the both the ABC fragment and the EFG fragment have been achieved. The fused tetrahydrofuran triad core of the ABC fragment has been synthesized via a base-mediated diepoxide cascade. The challenging 6,7,6 framework of the EFG fragment has been achieved through an intramolecular reductive cyclization reaction. With successful routes to the ABC and EFG cores in hand, current work is focused on elaboration of these intermediates to the desired Wittig coupling partners en route to the first total syntheses of tamulamides A and B ... [diagrams].</Abstract>
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