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Synthesis 2001(7): 1043-1048
DOI: 10.1055/s-2001-14570
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Improved Synthesis of (3S,12S)-N ¹ ,N 14-Diethyl-3,12-dihydroxy-homospermine, a Polyamine Analogue Therapeutic Agent

Raymond J. Bergeron*, Ralf Müller, James S. McManis, Guo Wei Yao, Guangfei Huang
Department of Medicinal Chemistry, University of Florida Health Science Center, Box 100485, Gainesville, Florida 32610-0485, USA
Fax: +(352)3928406; e-Mail: bergeron@mc.cop.ufl.edu;
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Publication History

Received 20 November 2000
Publication Date:
30 September 2004 (online)

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Abstract

The synthesis of a hydroxylated analogue of N 1,N 14-diethylhomospermine, (3S,12S)-N 1,N 14-diethyl-3,12-dihydroxyhomospermine, is described. The key step in the assembly of this homospermine derivative involves alkylation of N,N"-dibenzylputrescine with two equivalents of N-[(3S)-3,4-epoxybutyl]-N-ethyltrifluoromethanesulfonamide.

Key words

antitumor agents - chiral alcohols - epoxides - Mitsunobu reaction - polyamine analogue

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