A stereochemically controlled approach to the morphine alkaloids: racemization of 8,9-benzo-4,5-dihydro-6,7-pyrido[4,3-d] oxanin-3(2H)-ones

Graduate Thesis Or Dissertation

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Citeable URL: https://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/mw22v847r

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Attribute Name	Values
Creator	Runyan, Mark T.
Abstract	A method for the control of absolute stereochemistry in morphine syntheses has been demonstrated by the resolution and efficient racemization of the advanced morphine precursor , 9-methoxy-3-methyl-5,6-dihydro-3H-benzofuro[3,2-e]isoquinoline- 7(7aH)-one, I. This was accomplished by the facile coversion of optically resolved I to its ring opened form, 5,6,7,8-tetrahydro-10-methoxy-3-methyl-7-oxo[1]benzoxonino[ 6,7-c]pyridinium tosylate, II, (Equation I). Racemization via biaryl rotation in the oxaninone II was found to be very rapid. A detailed analysis of the biaryl rotation in II was completed by a dynamic NMR experiment. From this experiment, AG for the biaryl rotation was calculated to be 15.8 Kcal/mol.
Resource Type	Masters Thesis
Date Available	2013-07-09T15:32:09+00:00
Date Issued	1986-09-04
Degree Level	Master's
Degree Name	Master of Science (M.S.)
Degree Field	Chemistry
Degree Grantor	Oregon State University
Commencement Year	1987
Advisor	Weller, Dwight D.
Academic Affiliation	Chemistry
Non-Academic Affiliation	Oregon State University. Graduate School
Subject	Racemization Morphine
Rights Statement	Copyright Not Evaluated
Publisher	Oregon State University
Peer Reviewed	No
Language	English [eng]
Digitization Specifications	File scanned at 300 ppi (Monochrome) using ScandAll PRO 1.8.1 on a Fi-6670 in PDF format. CVista PdfCompressor 4.0 was used for pdf compression and textual OCR.
Replaces	http://hdl.handle.net/1957/40140

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