通过环状双[烯丙基]直接进入 erythronolide 途径。
Direct entry to erythronolides via a cyclic bis[allene].
机构信息
Department of Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.
出版信息
J Am Chem Soc. 2011 Sep 28;133(38):14968-71. doi: 10.1021/ja207496p. Epub 2011 Sep 6.
Abstract
The complexity and low tractability of antibiotic macrolides pose serious challenges to addressing the problem of resistance through semi- or total synthesis. Here we describe a new strategy involving the preparation of a complex yet tractable macrocycle and the transformation of this macrocycle into a range of erythronolide congeners. These compounds represent valuable sectors of erythromycinoid structure space and constitute intermediates with the potential to provide further purchase in this space. The routes are short. The erythronolides were prepared in three or fewer steps from the macrocycle, which was prepared in a longest linear sequence of 11 steps.
摘要
抗生素类大环内酯类的复杂性和低反应性给通过半合成或全合成来解决耐药性问题带来了严重的挑战。在这里，我们描述了一种新的策略，涉及到复杂但可处理的大环的制备以及将该大环转化为一系列红霉素类似物。这些化合物代表了红霉素结构空间的有价值的部分，并且是具有在该空间中进一步探索潜力的中间体。路线很短。从大环内酯类中通过三到四个步骤即可制备得到赤霉素，而大环内酯类则通过最长的 11 步线性序列制备得到。
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2
Collective synthesis of natural products by means of organocascade catalysis.通过有机级联催化对天然产物进行集体合成。
Nature. 2011 Jul 13;475(7355):183-8. doi: 10.1038/nature10232.
3
An efficient synthesis of loline alkaloids.洛林生物碱的高效合成。
Nat Chem. 2011 Jun 19;3(7):543-5. doi: 10.1038/nchem.1072.
4
Spirodiepoxide-based cascades: direct access to diverse motifs.基于螺环二环氧丙烷的级联反应：直接构建多样的结构基序。
Org Lett. 2011 Jul 1;13(13):3352-5. doi: 10.1021/ol201101e. Epub 2011 Jun 7.
5
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ACS Med Chem Lett. 2011 Jan 13;2(1):68-72. doi: 10.1021/ml1002184.
6
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