verruculogen and indole

verruculogen has been researched along with indole* in 1 studies

Other Studies

1 other study(ies) available for verruculogen and indole

ArticleYear
Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C-H Borylation.
    Journal of the American Chemical Society, 2015, Aug-19, Volume: 137, Issue:32

    Verruculogen and fumitremorgin A are bioactive alkaloids that contain a unique eight-membered endoperoxide. Although related natural products such as fumitremorgins B and C have been previously synthesized, we report the first synthesis of the more complex, endoperoxide-containing members of this family. A concise route to verruculogen and fumitremorgin A relied not only on a hydroperoxide/indole hemiaminal cyclization, but also on the ability to access the seemingly simple starting material, 6-methoxytryptophan. An iridium-catalyzed C-H borylation/Chan-Lam procedure guided by an N-TIPS group enabled the conversion of a tryptophan derivative into a 6-methoxytryptophan derivative, proving to be a general way to functionalize the C6 position of an N,C3-disubstituted indole for the synthesis of indole-containing natural products and pharmaceuticals.

    Topics: Catalysis; Chemistry Techniques, Synthetic; Indenes; Indoles; Iridium; Molecular Structure; Tryptophan

2015