Dictyodendrin B, C, and E
FÃ¼rstner, Domostoj, Scheiper. JACS, 2006, ASAP. DOI: 10.1021/ja0617800
Feeling a little rusty with your heterocyclic chemistry? The FÃ¼rstner group at the MPI Muelheim seem to know theirs pretty good, with totaly syntheses of Dictyodendrins B, C and E. Differing only by the oxidation levels and the substituents on the C-2 carbon (a ketone sidechain in Dictyodendrin B), their approach allows access to all three.
Their work contains several remarkable transformations, starting with the low-valent Ti convertion of ketoamides to indole derivatives:
Also worth of note is their following transformation, which performed a 6Ï€ electrocyclisation. By using catalytic Pd/C and nitrobenzene, the product aromatised in-situ, leading to a common precursor.
Also containing an impressive benzylic Suzuki coupling and subsequent oxidation, this paper’s definately worth a read!