Synthesis of the antifungal macrolide antibiotic (+)-roxaticin
Synthesis of the antifungal macrolide antibiotic (+)-roxaticin
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DOI：
10.1021/ja027638q
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发表时间：
2003-09-10
影响因子：
15
通讯作者：
Connell, BT
中科院分区：
文献类型：
--
作者：
Evans, DA;Connell, BT
完成了抗真菌大环内酯类抗生素罗沙替星的全合成。该合成主要依赖于羟醛和定向还原步骤来构建天然产物中存在的扩展的1，3-多元醇阵列。三个主要的nonpolyene含有片段组装，然后偶联使用Julia烯化和甲基酮羟醛加成反应。通过一系列的功能化反应，将敏感的多烯引入，得到了保护的罗沙替星开环酸，并以良好的产率进行了内酯化。酸性脱保护完成了罗沙替星的聚合合成。
The total synthesis of the antifungal macrolide antibiotic roxaticin has been accomplished. The synthesis relies principally on aldol and directed reduction steps to construct the extended 1,3-polyol array present in the natural product. Three principal nonpolyene containing fragments were assembled and then coupled using Julia olefination and methyl ketone aldol addition reactions. A series of functionalization reactions incorporated the sensitive polyene and provided the protected roxaticin seco-acid, which was lactonized in good yield. Acidic deprotection completed this convergent synthesis of roxaticin.