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PROGRESS TOWARDS THE TOTAL SYNTHESIS OF THE ANTIFUNGAL NATURAL PRODUCT (-)-PRAMANICIN by Christopher Gerth Meyer A Thesis Presented to the FACULTY OF THE GRADUATE SCHOOL UNIVERSITY OF SOUTHERN CALIFORNIA In Partial Fulfillment of the Requirements for the Degree MASTER OF SCIENCE (CHEMISTRY) August 2007 Copyright 2007 Christopher Gerth Meyer
Object Description
| Title | Progess towards the total synthesis of the antifungal natural product (-)-pramanicin |
| Author | Meyer, Christopher Gerth |
| Author email | christgm@usc.edu |
| Degree | Master of Science |
| Document type | Thesis |
| Degree program | Chemistry |
| School | College of Letters, Arts and Sciences |
| Date defended/completed | 2007-06-15 |
| Date submitted | 2007 |
| Restricted until | Unrestricted |
| Date published | 2007-08-01 |
| Advisor (committee chair) | Jung, Kyung Woon |
| Advisor (committee member) |
Petasis, Nicos A. Prakash, G.K. Surya |
| Abstract | Progress towards the total synthesis of the antifungal natural product (-)-pramanicin and efficient synthesis of its side chain, (E)-4,5-epoxy-2-tetradecenoic acid, are reported. (-)-Pramanicin consists of a functionalized lipophilic side chain bound to a chiral gamma-lactam head group. The key synthetic steps include: (i) oxygen-promoted palladium-catalyzed cross-coupling of an aliphatic alkenyl-boron compound with methyl acrylate, (ii) stereo- and regioselective monoepoxidation of the resultant diene, (iii) rhodium(II)-catalyzed intramolecular C-H insertion of an alpha-diazoacetamide to afford a bicyclic gamma-lactam, and (iv) lithium diisopropylamide promoted condensation of an alpha,beta-unsaturated, gamma,delta-epoxy aldehyde with the bicyclic gamma-lactam. |
| Keyword | total synthesis; natural product; Shi epoxidation; C-H insertion; Aldol reaction; antifungal; pramanicin; gamma-lactam |
| Language | English |
| Part of collection | University of Southern California dissertations and theses |
| Publisher (of the original version) | University of Southern California |
| Place of publication (of the original version) | Los Angeles, California |
| Publisher (of the digital version) | University of Southern California. Libraries |
| Type | texts |
| Legacy record ID | usctheses-m738 |
| Rights | Meyer, Christopher Gerth |
| Repository name | Libraries, University of Southern California |
| Repository address | Los Angeles, California |
| Repository email | http://www.usc.edu/isd/libraries/services/ask_a_librarian/email/ |
| Filename | etd-Meyer-20070801 |
| Archival file | uscthesesreloadpub_Volume40/etd-Meyer-20070801.pdf |
Description
| Title | Page 1 |
| Full text | PROGRESS TOWARDS THE TOTAL SYNTHESIS OF THE ANTIFUNGAL NATURAL PRODUCT (-)-PRAMANICIN by Christopher Gerth Meyer A Thesis Presented to the FACULTY OF THE GRADUATE SCHOOL UNIVERSITY OF SOUTHERN CALIFORNIA In Partial Fulfillment of the Requirements for the Degree MASTER OF SCIENCE (CHEMISTRY) August 2007 Copyright 2007 Christopher Gerth Meyer |
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