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Toward Palau'amine: Hg(OTf)(2)-Catalyzed Synthesis of the Cyclopentane Core

机译:面向帕劳胺:Hg(OTf)(2)催化的环戊烷核心的合成

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摘要

The pyrrole–imidazole alkaloids, which comprise a large family of natural products, have received a great deal of attention due to their potent biological activities and tremendous structural diversity.[1] Palau’amine (1) was originally isolated from a sponge, Stylotella agminata, in 1993 by Scheuer as a novel class of the pyrrole–imidazole alkaloid.[2]Since the initial disclosure of its proposed structure (1a),palau’amine (1; Figure 1) has been an attractive synthetic target because of its intriguing molecular architecture and significant biological properties such as antifungal, antitumor,and immunosuppressive activities. However, according to several groups, the originally proposed structure 1a was recently revised as 1b, which instead possesses the indicated the trans-D/E ring junction and the b-chlorine substitu-ACHTUNGTRENUNGent.[3,5e, g] The noteworthy structural features of palau’amine include: two guanidine moieties, a fused polycyclic system with a spiro cycle, a fully substituted complex cyclopentane ring, and eight contiguous stereogenic centers including a nitrogen-substituted quaternary carbon center.
机译:吡咯-咪唑生物碱,包括大量的天然产物,由于其强大的生物活性和巨大的结构多样性而受到了广泛的关注。[1] Palau'amine(1)最初是Scheuer于1993年从海绵Stylotella agminata中分离出来的,是一类新颖的吡咯-咪唑生物碱。[2]自从首次提出其结构(1a)以来,palau'amine( 1;图1)由于其有趣的分子结构和重要的生物学特性(例如抗真菌,抗肿瘤和免疫抑制活性)而成为有吸引力的合成靶标。但是,根据几个小组,最初提议的结构1a最近被修改为1b,它具有所示的反式D / E环结和b-氯取代的ACHTUNGTRENUNGENT。[3,5e,g]值得注意的结构帕劳胺的特征包括:两个胍基部分,具有螺环的稠合多环系统,完全取代的复杂环戊烷环和八个连续的立体异构中心,包括一个氮取代的季碳中心。

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