Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels-Alder Methodology.
Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels-Alder Methodology.
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使用不对称催化杂狄尔斯-阿尔德方法全合成 (R)-二氢猕猴桃内酯和 (R)-猕猴桃内酯。
DOI：
10.1021/jo971528y
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发表时间：
1998
期刊：
影响因子：
--
通讯作者：
K. A. Jørgensen
中科院分区：
文献类型：
--
作者：
Sulan Yao;M. Johannsen;R. Hazell;K. A. Jørgensen
报道了天然双环内酯（R）-二氢猕猴桃内酯和（R）-猕猴桃内酯的全合成。合成的关键步骤是铜（II）-双恶唑啉催化的环二烯与乙醛酸乙酯的杂Diels-桤木反应，以高产率和非常高的区域选择性、非对映选择性和对映选择性得到杂Diels-桤木产物。全合成通过中间体进行，该中间体也具有一系列其他天然产物的潜力。关键中间体的结构经X射线衍射分析确证。
The total synthesis of the naturally occurring bicyclic lactones (R)-dihydroactinidiolide and (R)-actinidiolide is presented. The key step in the syntheses is the copper(II)-bisoxazoline-catalyzed hetero-Diels-Alder reaction of a cyclic diene with ethyl glyoxylate giving the hetero-Diels-Alder product in high yield and with very high regio-, diastereo-, and enantioselectivity. The total syntheses proceed via an intermediate, which also has the potential for a series of other natural products. The structure of the key intermediate is confirmed by X-ray analysis.