Synthetic approach to analogues of the original structure of sclerophytin A
Synthetic approach to analogues of the original structure of sclerophytin A
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DOI：
10.1021/jo016246j
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发表时间：
2002-09-20
影响因子：
3.6
通讯作者：
Pontillo, J
中科院分区：
文献类型：
--
作者：
Jung, ME;Pontillo, J
描述了一种获得硬苔素A原始结构类似物的途径。二脱氧核桃基腈10a，b（由谷氨酸制备）的β -异头物转化为甲基酮11。在乙醚/三甲胺中加入硅基化的乙酰醚，主要得到22a。与甲基卤化物烷基化和臭氧分解得到酮24，然后通过加氢和第二次臭氧分解转化为酮醛26。两步醛醇法得到了所需的3-吡咯酮27，总收率很高。然而，几种将烯酮27转化为所需的硬苔素类似物2的方法都失败了。
A route to analogues of the original structure of sclerophytin A is described. The beta-anomer of dideoxyribosyl nitriles 10a,b (prepared from glutamic acid) was converted into the methyl ketone 11. Addition of a silylated acetylide to 11 in diethyl ether/trimethylamine gave mainly 22a. Alkylation with methallyl halide and ozonolysis gave the ketone 24, which was then converted by hydrogenation and a second ozonolysis into the keto aldehyde 26. A two-step aldol process afforded the desired 3-pyrone 27 in good overall yield. However, several methods for the conversion of this enone 27 into the desired sclerophytin analogue 2 failed.