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 Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/mw22v847r

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  • 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.
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