An asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: An efficient approach to the enantioselective synthesis of (+)-laurencin
An asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: An efficient approach to the enantioselective synthesis of (+)-laurencin
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DOI：
10.1021/ja990421k
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发表时间：
1999-06-23
影响因子：
15
通讯作者：
Choy, AL
中科院分区：
文献类型：
--
作者：
Crimmins, MT;Choy, AL
描述了一种策略，通过合并不对称羟醛加成与环给药复分解反应的羟基乙酸酯的不对称羟醛加成的中环环醚的不对称选择性建设。七元环、八元环和九元环的环醚可通过闭环复分解而容易地获得，而无需环状构象约束，通过利用非环状构象偏置的笨拙效应。利用羟醛-复分解反应合成了红藻代谢产物八元醚（+）-劳伦辛。
A strategy is described for the enantioselective construction of medium-ring cyclic ethers by merging the asymmetric aldol addition of glycolates with a ring-dosing metathesis reaction. Cyclic ethers of seven-, eight-, and nine-membered rings are readily available through a ring-closing metathesis without cyclic conformational constraints, by exploiting the acyclic conformational bias of the gauche effect. A short formal synthesis of the eight-membered ether (+)-laurencin, a red algae metabolite, has been accomplished utilizing the aldol-metathesis combination.