The Journal of Organic Chemistry

The chemistry of naturally occurring polyamines. 6. Efficient syntheses of N1-and N8-acetylspermidine

CM Tice, B Ganem

Index: Tice, Colin M.; Ganem, Bruce Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 2106 - 2108

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Citation Number: 18

Abstract

in the equatorial position (hence indistinguishable from the label at C-2 of l), the deuterium at C-2 of 3 is axial and easily quantifiable. The 2: l ratio for Cl/C-2, proves that the hydroxyl epimerization results from ketone reduction by lithium aluminum deuteride. These results suggest that caution should be observed before using epoxide opening by lithium aluminum deuteride as a means of incorporating a stereospecific isotopic label in a cyclic system.