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Studies Directed Toward a Novel Route of Terpene Total Synthesis Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1972 Studies Directed Toward a Novel Route of Terpene Total Synthesis. Elucidation of Structure and Reactivity of Some Substituted Tricyclo(6.2.1.0(2,7))-Undecan-3-Ones. Charles Sidney Aaron Sr Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Aaron, Charles Sidney Sr, "Studies Directed Toward a Novel Route of Terpene Total Synthesis. Elucidation of Structure and Reactivity of Some Substituted Tricyclo(6.2.1.0(2,7))-Undecan-3-Ones." (1972). LSU Historical Dissertations and Theses. 2189. https://digitalcommons.lsu.edu/gradschool_disstheses/2189 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 dissertation was produced from a microfilm copy of the original document. While the most advanced technological means to photograph and reproduce this document have been used, the quality is heavily dependent upon the quality of the original submitted. The following explanation of techniques is provided to help you understand markings or patterns 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 thru an image and duplicating adjacent pages to insure you complete continuity. 2. When an image on the film is obliterated with a large round black mark, it is an indication that the photographer suspected that the copy may have moved during exposure and thus cause a blurred image. You will find a good image of the page in the adjacent frame. 3. When a map, drawing or chart, etc., was part of the material being photographed the photographer followed a definite method in "sectioning" the material. It is customary to begin photoing at the upper left hand corner of a large sheet and to continue photoing from left to right in equal sections with a small overlap. If necessary, sectioning is continued again — beginning below the first row and continuing on until complete. 4. The majority of users indicate that the textual content is of greatest value, however, a somewhat higher quality reproduction could be made from "photographs" if essential to the understanding of the dissertation. Silver prints of "photographs" may be ordered at additional charge by writing the Order Department, giving the catalog number, title, author and specific pages you wish reproduced. University Microfilms 300 North Zeeb Road Ann Arbor, Michigan 48106 A Xerox Education Company Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. 72-28,323 AARON, Sr., Charles Sidney, 1943- STUDIES DIRECTED TOWARD A NOVEL ROUTE OF TERPENE TOTAL SYNTHESIS. ELUCIDATION OF STRUCTURE AND REACTIVITY OF SOME SUBSTITUTED TRICYCL0C6.2.1.0*??]-UNDECAN-3-ONES. The Louisiana State University and Agricultural and Mechanical College, Ph.D., 1972 Biochemistry University Microfilms, A XEROX Company, Ann Arbor, Michigan Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. STUDIES DIRECTED TOWARD A NOVEL ROUTE OF TERPENE TOTAL SYNTHESIS. ELUCIDATION OF STRUCTURE AND REACTIVITY OF SOME SUBSTITUTED TRICYCL0[6.2.1.02'7]_uNDECAN-)-0NES. 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 Biochemistry by Charles Sidney Aaron, Sr. B.S., Louisiana Polytechnic Institute, I968 May 1972 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. PLEASE NOTE: Some pages may have indistinct print. Filmed as received. University Microfilms, A Xerox Education Company Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. To my wife, Belle, and my children, Melanie and Charles. Without their love, understanding and confidence, I could never have come as far as I have Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ACKNOWLEDGEMENT The author would like to thank Professor G.E. Risinger, under whose direction this work was performed, for his patience in the direction of this research. Sincere thanks and appreciation are also extended to the members of the author’s advisory committee whose counsel was always freely given; Dr. R.S. Allen, Dr. C.D. Callihan, Dr. S. Chang and Dr. F.K. Cartledge. In addition, special thanks go to Mr. Bill Wegner, Mr. Ralph Seab, and Mrs. Cheryl White (all of whom are members of the Chemistry Department Staff, Louisiana State University, Baton Rouge). This grateful acknowledge­ ment is the only means of compensation which the author is able to offer to them for their untiring and generous efforts on his behalf. Dr. L. Green is most gratefully acknowledged for her "laying of the groundwork" for this project and for her generosity in supplying the author with samples of several of the compounds discussed herein. Financial assistance by the National Institutes of Health during the period I968 - 1970 is gratefully acknowledged. The financial support provided the author during 19?0 - 1971 hy the Louisiana State University is also gratefully acknowledged. 11 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. TABLE OF CONTENTS Page ACKNOWLEDGEMENT.................................................. ü LIST OF TABLES................................................... vii LIST OF FIGURES................................ viii LIST OF SPECTRA.................................................. xi ABSTRACT........................................................ xiil I. INTRODUCTION.............................................. 1 II. EXPERIMENTAL............................................... I9 A. Preparation of Bicyclo[2.2.l]hept-5-ene-2-carboxylic Acid (I)............................................... 20 B. Preparation of $-Iodo-6-hydroxy-bicyclo[2.2.l]heptane- 2-car boxy lie Acid Lactone (II)........................* 2 3 C. Preparation of endo-Bicyclo[2,2.l]hept-5-ene-2- carboxylic Acid^'^IIl)............................... 23 D. Preparation of Methyl Bicyclo[2.2. l]hept-5-ene-en^- 2-carboxylate (lll) .................................. 2 k E. Preparation of endo-2-Diphenylhydroxymethyl-bicyclo- [2.2.1]hept_3_e;rTlV). ........................ 25 F. Preparation of endo;-6-Diphenylhydroxymethyl-3- bicyclo[2.2.l]heptan-5-one (VIII) .................... 26 G. 2-Diphenylmethylenebicyclo[2.2.l]heptan-5“One (IX). 27 1. Preparation........................................27 2. Oxidation..........................................29 a. With Potassium Permanganate................... 29 b. With Ozone..................................... 29 H. Preparation of 2-Diphenylmethylenebicyclo[2.2.l]- heptane ( X ) ........................................... ^ 0 I. Preparation of endo-6-Diphenylhydroxymethyl-2-bicyclo- [2 .2 .1] heptanonZ'^XI ) ................................. 3 I J. Preparation of endo^6-Diphenylhydroxymethyl-endo^2- bicyclo[2.2.l]heptanol (XXV)...........................32 K. Preparation of 2,6-Bicyclo[2.2.l]heptanecarbolactone (XXIV)................................................. 33 iii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Page L. Preparation of 5“Bromo-8,8-diphenyl-7-oxatrlcyclo- [6.1.0.0*'8]nonane (V) ............. 35 M. Preparation of 8,8-Diphenyl-7-oxatrlcyclo[2.2.2^'1]- nonane (Vl). ...... ................... ..... 36 N. Preparation of 8,8-Diphenyl-7-oxatricyclo[2.2.2^^®.1]- nonane (Vll)................................... 36 0. Preparation of endo-Tricyclo[6.2.1.0^^^]undeca-4, 9- dien-3,6-dione 37 P. Preparation of endo-Tricyclo[6.2.1.0^'’^]undec-9-en- 3.6-dione (XIIl) .................................... 38 Q. Preparation of en^-Tricyclo[6.2.1.0^^^]undec-9-en- 3.6-diol (XIV) ...................................... 39 R. Preparation of lO-Bromo-6,9-6P°)^y-6nd^tricyclo- [6.2 .1.0^’^]undecan-3 -ol (XV)................... 59 S. Preparation of lO-Bromo-6,9-6poxy-endo-tricyclo- [6.2.1.0^^^]undecan-3“One (XVl). T .......... 40 T. Preparation of 6,9-epoxy-tetracyclo[4.2.1.0^^ ^.0^^ ^°]- undecan-3-one (XVII) ............ 4l U. The Ethylene Glycol Mono-ketal of end^Tricyclc- [6.2.1.0^^]undec-9-en-3,6-dione (XXI)............... 42 1. Preparation........................................42 2. Attempted Annélation............................. 42 V. Preparation of lO-Bromo-6,9-6poxy-6-hydroxy-end^ tricyclo[6.2.1.0^’^]undecan-3-one (XVIIl)............. 43 W. Preparation of 9-&%RrHydroxytetracyclo[6.2.1. undecan-3; 6-dione (XIX)......................... 44 X. Preparation of 9__gyjv,-Benzoyltetracyclo[6.2.1.0^.0^^]- undecan-3,6-dione (XX) .............................. 44 Y. Preparation of 9"Syn-Benozyltetracyclo[6.2.l.O^^.O^^®] undecan-3 ,6-diol ^Jctll)............................... 46 Z. Spectra.................................... .... 46 III. DISCUSSION.............................................
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