Stereoselectivity questions in the synthesis of wikstromol.
Stereoselectivity questions in the synthesis of wikstromol.
复制标题
wikstromol 合成中的立体选择性问题。
DOI：
10.1021/np50072a034
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发表时间：
1990
影响因子：
5.1
通讯作者：
Fry,DF
中科院分区：
文献类型：
--
作者：
Belletire,JL;Ho,DM;Fry,DF
虽然Davis氧氮丙啶试剂通常基于简单的空间考虑提供氧化产物，但当用于设计天然产物合成策略时，该概念似乎具有一些限制。因此，已经发现了一个实例，其中观察到的烯醇化物氧化的立体选择性是“异常的”。所讨论的系统涉及在具有高度氧化的芳环的木酚素丁内酯上进行的烯醇化物氧化。除了建立这种氧化过程和确认wikstromol和相关木脂素的拟议结构，wikstromol立体异构体的单晶X射线研究提供了与“天然”异构体比较的补充数据。
While the Davis oxaziridine reagent generally affords oxidation products based on simple steric considerations, this concept appears to have some limitations when used to design natural product synthetic strategies. Thus, an example has been found in which the observed stereoselectivity of an enolate oxidation is “anomalous.” The system in question in-volves an enolate oxidation performed on a lignan butyrolactone having highly oxygenated aromatic rings. Besides establishing the course of this oxidation and confirming the proposed structure of wikstromol and related lignans, a single-crystal X-ray study on a wikstromol stereoisomer provides complementary data for comparison with the" natural” isomer.