The Enantiospecific Total Syntheses of Adda and Nodularin

The unusual amino acid (2S, 3S, 4 E, 6E, 8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid (Adda) is a structural component of nodularin that has been reported to be necessary for biological activity. The complexity of Adda has hindered the completion of structure activity relationship (SAR) studies. This work has focused on development of procedures to synthesize Adda. As a result, novel methodology has been developed and employed to synthesize N -Boc-Adda in 40% overall yield in a 13 step linear synthesis. A convergent synthesis of N-Boc Adda was developed that provided N-Boc-Adda in 31% overall yield after 16 steps. Both procedures supply the N-Boc-Adda in yields that are several times higher than the best syntheses from commercially available material reported to date. These procedures for the synthesis of N-Boc-Adda should facilitate development of SAR studies to elucidate roles of protein phosphatases in tumor promotion or suppression.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2015

Author dc:creator

• Pearson, Jason Clay

Contributors dc:contributor

• Rinehart, Kenneth L., Jr.

• Chemistry, Organic

Language dc:language

eng

Identifier

(MiAaPQ)AAI9955655

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84468