Total Synthesis of Macroviracin D (BA-2836-4)

Jacek Mlynarski; Juliaza Ruiz-Caro; Alois Furstner

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Total Synthesis of Macroviracin D (BA-2836-4)

机译：Macroviracin D（BA-2836-4）的全合成

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The first total synthesis of the complex glycolipid macroviracin D (BA-2836-4) (1) is described.This anti-virally active metabolite isolated from the mycelium extracts of Streptomyces sp.BA-2836 incorporates a unique 46-membered macrodilactone motif decorated with glycosylated fatty acid appendices.Compound 1 consists of three identical subunits which are closely related to one of the segments found in cycloviracin B_1 (2),another antiviral glycoconjugate previously synthesized in our laboratory.Key steps of the synthesis route to 1 involve the stereose-lective,ligand-controlled addition of the functionalized diorganozinc derivative 9 to aldehydes 8a,b,a series of beta-selective glycosidation reactions using appropriately protected trichloroacet-imidate donors,and three esterifica-tions via the Yamaguchi method;one of them is performed intramolecularly to forge the macrocyclic lactone ring of the target in 89% isolated yield.This total synthesis also firmly establishes the absolute configuration of the sub-units of compound 1 as 3R,17S,23R.

机译：首次描述了复杂的糖脂大病毒素D（BA-2836-4）（1）的首次合成，该分离自链霉菌sp.BA-2836菌丝体提取物中的抗病毒活性代谢产物具有独特的装饰性46元巨双内酯基序化合物1由三个相同的亚基组成，这些亚基与在环病毒素B_1（2）中发现的一个片段紧密相关，后者是我们实验室中先前合成的另一种抗病毒糖缀合物。合成1的关键步骤涉及立体异构体选择性，配体控制地将官能化的二有机锌衍生物9添加到醛8a，b中，使用适当保护的三氯乙酸亚氨酸酯供体进行一系列的β选择性糖基化反应，并通过Yamaguchi方法进行三个酯化;其中一个进行在分子内以89％的分离产率构建目标的大环内酯环。化合物1亚基的构型为3R，17S，23R。

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《Chemistry: A European journal》 |2004年第9期|共9页
作者
Jacek Mlynarski; Juliaza Ruiz-Caro; Alois Furstner;
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正文语种 eng
中图分类化学;
关键词
antiviral agents; carbohydrates; glycolipids; macrocycles; natural products;

机译：抗病毒剂;碳水化合物;糖脂;大环化合物;天然产物;

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1. Total Synthesis of Macroviracin D (BA-2836-4) [J] . Jacek Mlynarski, Juliaza Ruiz-Caro, Alois Furstner Chemistry: A European journal . 2004,第9期

机译：Macroviracin D（BA-2836-4）的全合成
2. Determination of Absolute Structure of Macroviracins by Chemical Synthesis [J] . Shunya Takahashi, Moritoshi Hosoya, Hiroyuki Koshino, Organic letters . 2003,第9期

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Total Synthesis of Macroviracin D (BA-2836-4)

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