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The chemical synthesis of indole terpenoids of structural and biological interests has attracted remarkable attention. Here we report an Eu(fod)3 -catalyzed indole conjugate addition reaction, which tolerates various acid-sensitive functional groups. A collection of indole terpenoid mimics have been prepared from natural product-derived α,β-unsaturated enones on the basis of this reaction. The further conversion of the indole adducts into more complex natural product-like molecules has also been demonstrated., (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.) more...

A unified and bioinspired oxidative cyclization strategy was used in the first total syntheses of naturally occurring 12-epi-hapalindole Q isonitrile, hapalonamide H, deschloro 12-epi-fischerindole I nitrile, and deschloro 12-epi-fischerindole W nitrile, as well as the structural revision of the latter. Hapalindoles H and Q were also synthesized., (© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.) more...

A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6π-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold. more...

The chemical synthesis of indole terpenoids of structural and biological interests has attracted remarkable attention. Here we report an Eu(fod)3-catalyzed indole conjugate addition reaction, which tolerates various acid-sensitive functional groups. A collection of indole terpenoid mimics have been prepared from natural product-derived α,β-unsaturated enones on the basis of this reaction. The further conversion of the indole adducts into more complex natural product-like molecules has also been demonstrated. [ABSTRACT FROM AUTHOR] more...