The synthesis of oxa-analogues and homologues of naturally occurring polyamines

被引:0
|
作者
Lin, PKT [1 ]
Kuksa, VA [1 ]
Maguire, NM [1 ]
机构
[1] Robert Gordon Univ, Sch Appl Sci, Aberdeen AB25 1HG, Scotland
来源
SYNTHESIS-STUTTGART | 1998年 / 06期
关键词
polyamines; oxa-analogues of polyamines; polyamine homologues; rearrangement; synthesis;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A number of polyamine era-analogues 14a-d, 19 have been synthesised. Spermidine era-analogues and homologues 14 were made from N-(aminooxypropyl)phthalimide 8a which was obtained either from the Fmoc-deprotection of N-[3-(Fmoc-amino)propoxy]phthalimide 4a or from the reaction between 3-bromopropylamine and N-hydroxyphthalimide, both reactions involving an unusual rearrangement mechanism. Sulphonated derivatives 9, 16, upon Mitsunobu condensation with N-protected 3-aminopropanol or N-alkylation with N-(bromoalkyl)phthalimides, afforded the fully protected spermidine and spermine oxa-analogues and homologues. Subsequent sequential deprotection gave spermidine analogues 14. Using the same strategy, spermine oxa-analogue 19 was synthesised.
引用
收藏
页码:859 / 866
页数:8
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