Memorial University DAI: Studies directed toward the total synthesis of longifolene

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Title	Studies directed toward the total synthesis of longifolene
Author	Bukownik, Rudolf Robert
Description	Thesis (M.Sc.) -- Memorial University of Newfoundland, 1985. Chemistry
Date	1984
Pagination	vii, 60 leaves : ill.
Subject	Terpenes--Synthesis; Diels-Alder reaction;
Degree	M.Sc.
Degree Grantor	Memorial University of Newfoundland. Dept. of Chemistry
Discipline	Chemistry
Language	Eng
Notes	Bibliography : leaves 58-60.
Abstract	This thesis describes studies directed toward the total synthesis of longifolene utilizing as a key step an intramolecular Diels-Alder cyclization. Different approaches for the construction of spiro[2.4]hepta-4, 6-dienes have been explored and a general route involving the fulvene 63 developed. Nucleophilic addition of methlylithium to this fulvene generates a cyclopentadiene anion in situ, which closes to the requisite cyclopropane system by epoxide ring opening to afford 65. This cyclopentadiene unit will thus serve as the ‘left-had portion' for the approach to longifolene which is outlined. Procedures for the preparation and introduction of a suitable ‘right-hand portion' have also been examined, these preliminary results have indicated the subtle blend of functionality and reactivity that will be required to generate the dienophilic unit. A suitable triene system 104 was synthesized (unfortunately in low yield) but under the conditions examined the desired Diels-Alder cyclization did not occur.
Type	Text
Resource Type	Electronic thesis or dissertation
Format	Image/jpeg; Application/pdf
Source	Paper copy kept in the Centre for Newfoundland Studies, Memorial University Libraries
Local Identifier	75331813
Rights	The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission.
Collection	Electronic Theses and Dissertations
Scanning Status	Completed
PDF File	(21.56 MB) -- http://collections.mun.ca/PDFs/theses/Bukownik_RudolfRobert.pdf
CONTENTdm file name	312659.cpd