A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid
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用于不对称合成 (-)-antrocin、()-asperolide C 和 (-)-trans-ozic 酸的手性池方法
DOI：
10.1039/c6cc06794h
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发表时间：
2016-01-01
影响因子：
4.9
通讯作者：
Yang, Zhen
中科院分区：
文献类型：
--
作者：
Li, Fu-Zhuo;Li, Shuang;Yang, Zhen
芳香族松香烷（+）-鼠尾草酸（4）的臭氧分解用于产生对映体纯形式的重要中间体，导致（-）-antrocin（1）的简单、简洁、易于放大和不对称合成。该方法不仅为（-）-antrocin（1）的合成提供了一种有效的途径，而且也可用于从天然芳香松香烷（+）-podocarpic acid（5）和（+）-dehydroabietic acid（6）合成光学纯的（+）-aspercine C（2）和（-）-trans-ozic acid（3）。这里提出的策略是使用天然存在的芳香族松香烷作为手性池的一个例子，并提供了一个帐户的萜类化合物的不对称合成。
Ozonolysis of aromatic abietane (+)-carnosic acid (4) is used to create an important intermediate in an enantiomerically pure form, resulting in a simple, concise, readily scalable, and asymmetric synthesis of (-)-antrocin (1). This strategy not only provides an efficient approach to (-)-antrocin (1) synthesis but can also be readily adopted for the syntheses of optically pure (+)-asperolide C (2) and (-)-trans-ozic acid (3) from the naturally abundant aromatic abietanes (+)-podocarpic acid (5) and (+)-dehydroabietic acid (6). The strategy presented here is an example of the use of naturally occurring aromatic abietanes as a chiral pool and offers an account of the asymmetric synthesis of terpenoids.