An Improved Synthesis of (3S,12S)-N¹,N14-Diethyl-3,12-dihydroxy-homospermine, a Polyamine Analogue Therapeutic Agent

Raymond J. Bergeron; Ralf Müller; James S. McManis; Guo Wei Yao; Guangfei Huang

doi:10.1055/s-2001-14570

PAPER

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;

Abstract

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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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Referenzen

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

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