Total synthesis of (-)-cylindrocyclophane F
Total synthesis of (-)-cylindrocyclophane F
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DOI：
10.1021/ja991538b
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发表时间：
1999-08-18
影响因子：
15
通讯作者：
Paone, D
中科院分区：
文献类型：
--
作者：
Smith, AB;Kozmin, SA;Paone, D
最近由摩尔及其同事从地衣种子植物中分离得到的Cylindrocyclophanes AF，1包含一个独特的天然产物家族，具有22-元[7，7]-对环芳环。尽管Cram和Steinberg在1951年首次合成了大量的环番化合物，但Cylindrocyclophanes是从天然来源中分离出来的第一个例子。结构归属，包括完整的相对和绝对立体化学，是基于广泛的NMR研究1b结合CD光谱和X射线晶体学。1a除了它们的新结构之外，圆柱环番还显示出对KB和LoVo肿瘤细胞系的体外细胞毒性。[1a]我们被它的结构和有希望的生物学特性所吸引，开始了一项针对它们的合成的计划。在此，我们首次公开了（-）-柱环蕃F的全合成
The cylindrocyclophanes AF, recently isolated by Moore and co-workers from Cylindrospermum licheniforme, 1 comprise a unique family of natural products possessing a 22-membered [7, 7]-paracyclophane ring. Although a wide variety of cyclophanes have been prepared2, 3 since their initial synthesis by Cram and Steinberg in 1951, 4 the cylindrocyclophanes represent the first examples isolated from a natural source. Structural assignments, including complete relative and absolute stereochemistry, were based on extensive NMR studies1b in conjunction with CD spectroscopy and X-ray crystallography. 1a In addition to their novel architecture, the cylindrocyclophanes display in vitro cytotoxicity against the KB and LoVo tumor cell lines. 1a Captivated both by the structure and the promising biological profile, we initiated a program directed at their synthesis. Herein, we disclose the first total synthesis of (-)-cylindrocyclophane F