Studies toward the total syntheses of tamulamides A and B

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].

Department dc:contributor.department

Massachusetts Institute of Technology. Department of Chemistry.

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2017

Author dc:creator

• Kelley, Elizabeth H. (Elizabeth Helen)

Advisor dc:contributor.advisor

• Timothy F. Jamison.

• Chemistry.

Statement dc:rights

• 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.

Licence dc:rights.uri

• http://dspace.mit.edu/handle/1721.1/7582

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/1721.1/109676

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/109676