Total Synthesis of (+)-Aberrarone
Yang Wang, Yongjian Su, Yanxing Jia
Abstract
The structurally intriguing diterpene (+)-aberrarone has been assembled in only 12 steps from the commercially available ( S, S )-carveol without protecting group manipulations. This concise synthesis features a Cu-catalyzed asymmetric hydroboration to generate the chiral methyl group, a Ni-catalyzed reductive coupling to link two fragments, and a Mn-mediated radical cascade cyclization to construct the triquinane system.
Topics & Concepts
ChemistryHydroborationDiterpeneStereochemistryTotal synthesisCascadeProtecting groupNitroCatalysisCombinatorial chemistryOrganic chemistryChromatographyAlkylSynthetic Organic Chemistry MethodsMarine Sponges and Natural ProductsChemical synthesis and alkaloids