Challenge palau'amine: Current standings
Challenge palau'amine: Current standings
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DOI：
10.2174/138527205774370531
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发表时间：
2005-10-01
影响因子：
2.6
通讯作者：
Lindel, T
中科院分区：
文献类型：
--
作者：
Jacquot, DEN;Lindel, T
来自海绵 Stylotella aurantium 的海洋天然产物 (-)-palau'amine 是全合成面临的最严峻的挑战之一。它具有应变的六环骨架，使当前的有机合成方法达到了极限。最近，几个研究小组采取了独立的方法，重点关注涉及潜在生物遗传关键代谢物 oroidin 的可能仿生方法。 Oroidin 是吡咯-咪唑生物碱的母体化合物。本文讨论了自 2003 年以来该领域的最新进展，概述了 4(5)-烯基咪唑二聚、非环化吡咯-咪唑生物碱、二溴法凯尔他汀、agelastatin 的全合成以及 Hymenialdisine 的最新进展。尽管帕劳胺尚未合成，但该系统已有一些原始方法，可提供具有生物活性的较小吡咯-咪唑生物碱，例如二溴法凯尔他汀和阿格司他汀 A。
The marine natural product (-)-palau'amine from the sponge Stylotella aurantium represents one of the toughest challenges to total synthesis. It possesses a strained hexacyclic skeleton which leads current methods of organic synthesis to their limit. Recently, several research groups have undertaken independent approaches, focussing on possibly biomimetic approaches involving the underlying biogenetic key metabolite oroidin. Oroidin is the parent compound of the pyrrole-imidazole alkaloids. In this review, recent developments in the field since 2003 are discussed, outlining progress on the dimerization of 4(5)-alkenylimidazoles, total syntheses of non-cyclized pyrrole-imidazole alkaloids, of dibromophakellstatin, agelastatin, and an update on hymenialdisine. Although palau'amine has not yet been synthesized, there are original approaches to the system which have afforded biologically active, smaller pyrrole-imidazole alkaloids such as dibromophakellstatin and agelastatin A.