The Enantiospecific Total Syntheses of Adda and Nodularin

Pearson, Jason Clay

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Description

Title

The Enantiospecific Total Syntheses of Adda and Nodularin

Author(s)

Pearson, Jason Clay

Issue Date

1999

Doctoral Committee Chair(s)

Rinehart, Kenneth L., Jr.

Department of Study

Chemistry

Discipline

Chemistry

Degree Granting Institution

University of Illinois at Urbana-Champaign

Degree Name

Ph.D.

Degree Level

Dissertation

Keyword(s)

Chemistry, Organic

Language

eng

Abstract

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.

Graduation Semester

1999

Type of Resource

text

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