De novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation
De novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation
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DOI：
10.1021/ol051383e
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发表时间：
2005-09-01
期刊：
影响因子：
5.2
通讯作者：
O'Doherty, GA
中科院分区：
文献类型：
--
作者：
Guo, HB;O'Doherty, GA
通过七至八步反应实现了对映选择性合成道蒙及其类似物。该途径依赖于非对映选择性钯催化的糖基化反应以形成异头键。通过酰基呋喃和炔丙基酮的Noyori还原引入了道曼酮的糖和糖苷配基部分的不对称性。高度非对映选择性的环氧化和还原开环建立了所需的C-2和C-4立体化学的道蒙。
The enantioselective syntheses of daumone and two analogues have been achieved in seven to eight steps. This route relies upon a diasteroselective palladium-catalyzed glycosylation reaction for the formation of the anomeric bond. The asymmetry of the sugar and aglycone portion of daumone were introduced by Noyori reduction of an acylfuran and a propargyl ketone. A highly diastereoselective epoxidation and reductive ring opening established the desired C-2 and C-4 stereochemistry of daumone.