The first enantioselective total synthesis of JBIR-03 and asporyzin C, indole diterpenoids of fungal origin exhibiting a range of pharmacologically important biological activities, has been accomplished from a known bicyclic keto alcohol in 13 and 14 steps, respectively. A hydroxy-directed cyclopropanation and Pd(II)-mediated indole ring formation were exploited as the key steps to obtain a pivotal pentacylic intermediate, which was converted into asporyzin C via chain elongation using cross-metathesis and then into JBIR-03 by Pd(II)-catalyzed tetrahydrofuran ring formation in an exclusively diastereoselective manner.

中文翻译：

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JBIR-03和Asporyzin C的全合成

JBIR-03和Asporyzin C（一种真菌来源的吲哚二萜类化合物，具有一系列药理上重要的生物活性）的首次对映选择性全合成已分别从已知的双环酮醇中分13步和14步完成。以羟基为导向的环丙烷化和Pd（II）介导的吲哚环的形成为关键步骤，以获取关键的五酰基中间体，该中间体通过交叉复分解通过链伸长转化为Asporyzin C，然后由Pd（J）转化为JBIR-03。 II）以非对映选择性的方式催化四氢呋喃环的形成。