Total synthesis of JBIR-03 and asporyzin C

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Abstract 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.

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