Organocatalytic asymmetric syntheses of inthomycins A, B and C
Organocatalytic asymmetric syntheses of inthomycins A, B and C
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DOI：
10.1039/c2ob26084k
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发表时间：
2012-10-28
影响因子：
3.2
通讯作者：
Hatakeyama, Susumi
中科院分区：
文献类型：
--
作者：
Yoshino, Madoka;Eto, Kohei;Hatakeyama, Susumi
从链霉菌（Streptomyces sp.）中分离的恶唑三烯类抗生素（+）-吲哚霉素A、（+）-吲哚霉素B和（-）-吲哚霉素C的全合成，通过利用金鸡纳香苷催化的不对称β-内酯合成及其与（E）-5-（3-（三丁基甲锡烷基）烯丙基）恶唑的无异构化Stille偶联，通过C1-C7（碘代二烯基）羟醛单元的高度对映体和立体选择性构建来实现。
The total syntheses of (+)-inthomycin A, (+)-inthomycin B and (-)-inthomycin C, the oxazole-triene antibiotics isolated from Streptomyces sp., have been accomplished via the highly enantio- and stereoselective construction of the C1-C7 (iododienyl)aldol units by taking advantage of a Cinchona alkaloid-catalyzed asymmetric P-lactone synthesis and their isomerisation-free Stille coupling with (E)-5-(3-(tributylstannyl)allyl)oxazole.