Synthesis of (+)- and (-)-Gossonorol and Cyclisation to Boivinianin B
Synthesis of (+)- and (-)-Gossonorol and Cyclisation to Boivinianin B
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DOI：
10.1002/ejoc.201000391
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发表时间：
2010-05-01
影响因子：
2.8
通讯作者：
Gibson, Susan E.
中科院分区：
文献类型：
--
作者：
Abecassis, Keren;Gibson, Susan E.
首次实现了棉酚的对映体选择性合成，总收率高，对映体选择性好，证明了一种新的合成对映体叔丁基醇的方法的有效性。对映体棉酚的环氧化和酸催化的环化反应得到了牛至草素B的非对映异构体混合物，这是自然界中发现的这种化合物的典型的非对映异构体混合物。非对映异构体的分离和对映体纯度的测定表明，在环氧化/环化反应过程中，棉酚的苯甲醇的立体化学完整性得以保持。
The first enantioselective synthesis of gossonorol has been achieved in good overall yield and excellent enantioselectivity, demonstrating the utility of a novel approach to enantiopure tertiary benzylic alcohols. Epoxidation of enantiopure gossonorol followed by acid-catalysed cyclisation gave a diastereoisomeric mixture of boivinianin B, typical of the diastereoisomeric mixtures of this compound found in nature. Separation of the diastereoisomers and determination of their enantiopurity revealed that the stereochemical integrity of the benzylic alcohol of gossonorol had been preserved during the epoxidation/cyclisation reaction.