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Universi^ Micrxsilms International 300 N 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.Tlie sign or “target” for pages apparently lacking from the document photographed is “ Missing Page(s)” . I f 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 o f 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 o f a large sheet and to continue from left to right in equal sections with small overlaps. I f 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. Universi^ MicrxSilms International 300 N. Zeeb Road Ann Arbor, Ml 48106 8426387 Galemmo, Robert Anthony, Jr. SYNTHETIC STUDIES ON THE STRUCTURE OF SENOXYDENE: A SEQUENTIAL ANNULATION APPROACH TO ANGULAR TRIOUINANE SYNTHESIS The Ohio Stale University Ph.D. 1984 University Microfilms i ntern eti 0n el300 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) 13(Fig. 1) 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 numbered ____________ . Text follows. 14. Curling and wrinkled pages______ 15. O t h e r _____________________________________ University Microfilms International SYNTHETIC STUDIES ON THE STRUCTURE OF SENOXYDENE: A SEQUENTIAL ANNULATION APPROACH TO ANGULAR TRiqUINANE SYNTHESIS DISSERTATION Presented, in Partial Fulfillm ent of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Robert Anthony Galemmo, J r ., B.A., M.S. ***** The Ohio State University 1984 Reading Committee Approved by Dr. Harold Shechter Dr. John S. Swenton Dr. Leo A. Paquette Dr. Leo A. Paquette, Advisor Department of Chemistry To my Mother and Father, for giving me what i t takes to see something through. ACKNOWLEDGEMENTS I wish to gratefully acknowledge the advice and support of Professor Leo Paquette while working under his direction. I am indebted to my many friends and associates in the Paquette group for their suggestions and technical assistance. Mary, B illy , Ken, Dan and Keith have been responsible for making my stay here a pleasant one. Several individuals have made contributions to the preparation of this manuscript. Ken, Keith, Geoff, Dan, Craig and John have helped to correct my atrocious grammar and spelling. Kay's stamina and endurance in typing this work has served us both w ell. Finally I wish to thank the staff of the Venetian for giving me a quiet place to write on sunny days. r r r VITA May 14, 1954 ................................ Born - Philadelphia, Pennsylvania 1976 ................................................ B.A., State University of New York, College at Potsdam, Potsdam, New York. 1977-1981 .................................... Teaching Associate, Department of Chemistry, The Ohio State University, Columbus, Ohio. 1981 ................................................ M.S., The Ohio State University, Columbus, Ohio. 1981-1984 ........................................ Research Associate, Department of Chemistry, The Ohio State University, Columbus, Ohio. MASTER THESIS The Preparation Of Components Of The 0-Anti genic Si de-Chain Of Pseudomonas Aeruginosa Type V Advisor: Professor Derek Horton PUBLICATIONS ”4.7.7-Trimethyl-cis-bicyclo[3.3.0]oct-3-en-2-one: A Potentially Useful Synthon for Triquinane Natural Products", Leo A. Paquette, Eugene Farkas and Robert A. Galemmo, J r ., J. Org. Chem., 46, 5434 (1981). "Preparative Routes to Methyl 2-acetamido-2,6-dideoxy-a-D-glucopyrano- side", Robert A. Galenmo, Jr. and Derek Horton, CarbohydT Res. , 119, 231 (1983). iv "Synthesis of the Alleged Structure of Senoxydene, the Triquinane Sesquiterpene Derived from Senecio Oxyodontus", Leo A. Paquette, Robert A. Galemmo, J r ., and James P. Springer, J. Am. Chem. Soc., 105, 6976 (1983). FIELD OF STUDY Organic Chemistry TABLE OF CONTENTS Page DEDICATION.......................................................................................................... 11 ACKNOWLEDGEMENTS .............................................................................................. I l l VITA ...................................................................................................................... Iv LIST OF FIGURES............................................................................................... 1x LIST OF TABLES.......................................................................................................x lll A CAVEAT FOR THE CHEMIST............................................................................... xlv CHAPTER I. The Angular Triquinane Sesquiterpenes 1. Introduction .................................................................................... 1 2. Angular Triqulnanes .................................................................... 2 3. Isocomene ........................................................................................ 3 3.1 Isolation and Natural Occurrence ................................ 3 3.2 Biogenesis.......................................................................... 5 3.3 Syntheses .............................................................................. 6 4. Sllphlnene........................................................................................ 10 4.1 Isolation and Natural Occurrence .................................... 10 4.2 Biogenesis.......................................................................... 11 4.3 Syntheses .............................................................................. 11 5. SI 1 phiperfolenes............................................................................ 15 5.1 Isolation and Natural Occurrence .................................... 15 5.2 Biogenesis.......................................................................... 16 5.3 Synthesis .............................................................................. 19 6. Rental e n e n e.................................................................................... 20 6.1 Isolation and Natural Occurrence .................................... 20 6.2 Biogenesis.......................................................................... 21 6.3 Syntheses .............................................................................. 23 v1 TABLE OF CONTENTS (Cont.) Page 7. Senoxydene ........................................................................................ 27 7.1 Isolation and Natural Occurrence ................................ 27 7.2 Biogenesis ........................................................................... 27 I I . Two Approaches to Senoxydene ( 56) Based Upon the Favorskii Reaction. 1. Statement of the Problem............................................................ 29 2. Elaboration of a Favorskii Reaction Product ..................... 30 2.1 Retrosynthesis and Methodology .................................... 30 2.2 Synthetic W ork ................................................................... 35 2.3 Previous Preparations of 6 6............................................ 39 3. Attempted Favorskii Ring Contraction of a Bicyclic Precursor ....................................................................................... 41 3.1 Retrosynthesis and Methodology .................................... 41 3.2 Synthetic W ork ................................................................... 43 I I I . The Total Synthesis of Angular Triquinane 5^: Alleged Senoxydene.
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