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首页> 外文期刊>Chemistry: A European journal >Total synthesis of branimycin: An evolutionary approach
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Total synthesis of branimycin: An evolutionary approach

机译：布雷尼霉素的全合成：一种进化方法

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The first total synthesis of the macrolactone antibiotic branimycin (4) has been described. The key disconnection leads to a cis-dehydrodecalone core and a polyketide side chain which are connected via organometallic addition. The dehydrodecalone core was targeted via altogether five different approaches featuring various kinds of chiral elements and ring-closing methodology. In the end the most successful method starting from diepoxynaphthalene 109 was chosen to carry on with the synthesis. Thus the oxygen functions and carbon appendages were introduced via organometallic desymmetrization reactions to generate epoxy ketone 107, to which vinyl iodide 11 was added after conversion into the organolithium species. The synthesis was completed by introducing the ester side chain via Michael addition and subsequent macrolactonization. Competitive approach: The first total synthesis of the macrolactone antibiotic branimycin is described (see figure). The dehydrodecalin core was targeted via five competing approaches featuring various kinds of chiral elements and ring-closing methodology. In this "Darwinian" struggle the most successful route emerged and led to the completion of the synthesis.
机译：已经描述了大内酯抗生素布雷尼霉素的首次全合成（4）。关键的断开导致通过有机金属加成连接的顺式-脱氢十氢萘酮核和聚酮侧链。脱氢癸酮的核心是通过五种不同的方法作为目标，这些方法具有各种手性元素和闭环方法。最后，选择了最成功的方法，从二环氧萘109开始进行合成。因此，经由有机金属脱对称反应引入氧官能团和碳附件，以生成环氧酮107，在转化成有机锂物质之后向其添加碘代乙烯11。通过经由迈克尔加成和随后的大内酯化引入酯侧链来完成合成。竞争性方法：描述了大内酯抗生素布雷尼霉素的第一个全合成（见图）。脱氢十氢化萘核心是通过五种竞争性方法进行靶向的，这些方法具有各种手性元素和闭环方法。在这场“达尔文主义”斗争中，最成功的路线出现了，并导致了合成的完成。

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