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New Sesquiterpene Lactones from the Genera Calea and Berlandiera (Asteraceae) and the Fragmentation Reactions of 1,3-Dihydroxyeudesmanolide Derivatives

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Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1983 New Sesquiterpene Lactones From the Genera Calea and Berlandiera (Asteraceae) and the Fragmentation Reactions of 1,3-Dihydroxyeudesmanolide Derivatives. Ihl Young Lee Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Lee, Ihl Young, "New Sesquiterpene Lactones From the Genera Calea and Berlandiera (Asteraceae) and the Fragmentation Reactions of 1,3-Dihydroxyeudesmanolide Derivatives." (1983). LSU Historical Dissertations and Theses. 3895. https://digitalcommons.lsu.edu/gradschool_disstheses/3895 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. INFORMATION TO USERS This reproduction was made from a copy of a document sent to us for microfilming. While the most advanced technology has been used to photograph and reproduce this document, the quality of the reproduction is heavily dependent upon the quality of the material submitted. The following explanation of techniques is provided to help clarify markings or notations which may appear on this reproduction. 1.The sign or “target” for pages apparently lacking from the document photographed is “Missing Page(s)”. If it was possible to obtain the missing page(s) or section, they are spliced into the film along with adjacent pages. This may have necessitated cutting through an image and duplicating adjacent pages to assure complete continuity. 2. When an image on the film is obliterated with a round black mark, it is an indication of either blurred copy because of movement during exposure, duplicate copy, or copyrighted materials that should not have been filmed. For blurred pages, a good image of the page can be found in the adjacent frame. If copyrighted materials were deleted, a target note will appear listing the pages in the adjacent frame. 3. When a map, drawing or chart, etc., is part of the material being photographed, a definite method of “sectioning” the material has been followed. It is customary to begin filming at the upper left hand comer of a large sheet and to continue from left to right in equal sections with small overlaps. If necessary, sectioning is continued again—beginning below the first row and continuing on until complete. 4. For illustrations that cannot be satisfactorily reproduced by xerographic means, photographic prints can be purchased at additional cost and inserted into your xerographic copy. These prints are available upon request from the Dissertations Customer Services Department. 5. Some pages in any document may have indistinct print. In all cases the best available copy has been filmed. University Microfilms International 300 N. Zeeb Road Ann Arbor, Ml 48106 8400127 Lee, Ihl Young NEW SESQUITERPENE LACTONES FROM THE GENERA CALEA AND BERLANDIERA (ASTERACEAE) AND THE FRAGMENTATION REACTIONS OF 1,3-DIHYDROXYEUDESMANOLIDE DERIVATIVES The Louisiana State University and Agricultural and Mechanical Col.Ph.D. 1983 University Microfilms International300 N. Zeeb Road, Ann Arbor, Ml 48106 PLEASE NOTE: In all cases this material has been filmed in the best possible way from the available copy. Problems encountered with this document have been identified here with a check mark V . 1. Glossy photographs or pages______ 2. Colored illustrations, paper or print______ 3. Photographs with dark background______ 4. Illustrations are poor copy_______ 5. Pages with black marks, not original copy_______ 6. Print shows through as there is text on both sides of page______ 7. Indistinct, broken or small print on several pages 8. Print exceeds margin requirements______ 9. Tightly bound copy with print lost in spine_______ 10. Computer printout pages with indistinct print______ 11. Page(s)____________lacking when material received, and not available from school or author. 12. Page(s)____________seem to be missing in numbering only as text follows. 13. Two pages n u mbered____________. Text fol lows. 14. Curling and wrinkled pages______ 15. Other_________________________________________________________________________ University Microfilms International NEW SESQUITERPENE LACTONES FROM THE GENERA CALEA AND BERLANDIERA (ASTERACEAE) AND THE FRAGMENTATION REACTIONS OF 1,3-DIHYDROXYEUDESMANOLIDE DERIVATIVES. A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy in The Department of Chemistry by Ihl Young Lee B.S., Kyung Puk National University, 1973 M.S., Seoul National University, 1976 August 1983 To my family ii ACKNOWLEDGEMENT I would like to express my sincere appreciation to my major professor, Nikolaus H. Fischer for his enthusiastic guidance and assistance through this research. The collection and identification of the various plants by Dr. 0. R. Wussow and Professor Lowell Urbatsch is greatly appreciated. Special thanks to Mrs. Helga Fischer for her technical assistance in the extraction of the many plant populations and to Dr. Frank Fronczek for the X-ray data. Also, extreme gratitude is extended to my husband and daughter, Ji- Eun, who have been spiritual support. Lastly the financial support received from the Coates Memorial Foundation is gratefully acknowledged. TABLE OF CONTENTS Page ACKNOWLEDGEMENTS................................................................................................ iii LIST OF TABLES.............................. ....................................................................... vii LIST OF FIGURES................................................................................................... viii LIST OF SCHEMES................................................................................................... xi ABSTRACT................................................................................................................... xii CHAPTER 1. Introduction 1.1 Systematic background in the genus Calea ............................................................................ 2 1.2 Sesquiterpene lactones in the genus Calea ............................................................................ 3 2. The isolation, structure elucidation, and chemistry of sesquiterpene lactones from Calea te rn ifo lia ............................................................................ 22 2.1 Isolation of tem ifo lin s, zexbrevin derivatives, atripliciolide derivatives, and 2,3-epoxycalein A ..................................................... 23 2.2 The structures of ternifolin derivatives 32 and 33 ..................................................... 29 2.3 Oxidation reactions of compounds 32 and 33 ........................................................................ 31 2.4 The structure of zexbrevin- type furenones 2.41. 9a-Acetoxyzexbrevin .......................................... 40 iv Page 2.42 83-Angeloyloxy-9a-hydroxy- calyculatolide and 9a-hydroxy- zexbrevin ................................................................... 41 2.5 The structure of atripliciolide derivatives..... ................................................................... 47 2.51 11,13-Dihydro-11a,13- epoxyatripliciolide-83-0-angelate and 11,13-di hydro-11 ci-13- epoxyatri pii ci oli de-83-0- methacrylate............................................................ 47 2.52 9 o-Hydroxy-11,13-dihydro- 11 a, 13-epoxyatri pi i ci ol i de 83-0- angel ate and 9a-hydroxy-l1,13-dihydro - 11 a ,13-epoxy-atri pii ci oli de-8 3-0- metacrylate.............................................................. 52 2.53 15-Hydroxy-l1,13-di hydro-11 a, 13-epoxyatripii ci oli de - 83-0-angelate .......................................................... 55 2.6 The tentative structure of 2,3-epoxycalein A.. 61 2.7 Epoxidation of calein A .................................................. 62 2.8 Experimental ........................................................................... 68 3. The isolation and structure elucidation of sesquiterpene lactones from Berlandiera texana and B. ly atra ....................................................... 76 3.1 Introduction ........................................................................... 77 3.2 Isolation of pumilin and 3a-epoxypumilin 77 v Page 3.3 The structure of pumilin ............................................... 78 3.4 The structure of 3a-epoxypumilin ............................. 84 3.5 Experimental ........................................................................... 91 4. Preparation and fragmentations of 1,3-dihydroxyeudesmanolide derivatives............. 94 4.1 Introduction ........................................................................... 95 4.2 Isolation of costunolide ................................................ 104 4.3 Reductive and oxidative modifications of costunolide ........................................ 107 4.4 Cyclization reactions of germacranolides 108 4.5 Preparation and chemical transformations of eudesmanolides ............................ 110 4.6 Experimental ........................................................................... 137 REFERENCES..............................................................................................................
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