Total synthesis of papulacandin D
Total synthesis of papulacandin D
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DOI：
10.1021/ja070071z
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发表时间：
2007-03-14
影响因子：
15
通讯作者：
Kobayashi, Tetsuya
中科院分区：
文献类型：
--
作者：
Denmark, Scott E.;Regens, Christopher S.;Kobayashi, Tetsuya
报道了抗真菌剂 papulacandin D 的全合成。该分子是一大类具有显着抗真菌活性的 C-芳基糖苷的代表。该合成策略将分子分成两个几乎相等的亚基：芳基糖苷和 18 碳脂肪酸侧链。关键的战略转变是（1）受保护的葡糖硅烷醇的钯催化、基于有机硅烷醇酯的交叉偶联，以及（2）使用烯丙基三氯硅烷对二烯醛进行催化对映选择性烯丙基化。该合成总共通过 31 个步骤从商业原材料完成，得到超过 50 毫克的天然产物。
A total synthesis of the antifungal agent papulacandin D is reported. The molecule is representative of a large class of C-aryl glycosides that exhibit significant antifungal activity. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the arylglycoside and 18-carbon fatty acid side chain. The key strategic transformations are (1) the palladium catalyzed, organosilanolate-based cross-coupling of a protected glucal silanol and (2) a catalytic enantioselective allylation of a dienal using allyltrichlorosilane. The synthesis was accomplished in 31 steps overall from commercial starting materials to afford over 50 mg of the natural product.