Dictyodendrin B, C, and E
Fürstner, Domostoj, Scheiper. JACS, 2006, ASAP. DOI: 10.1021/ja0617800
Feeling a little rusty with your heterocyclic chemistry? The Fürstner 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!
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The reactant in the first scheme below the title compound (the McMurry coupling to form the indole) has a methyl group on the cinnamide, while the product has a methoxy group on the derived styryl chain (in the correct position to form the hydroxy group of the product) – the methyl group in the reactant should be a methoxy group. Sorry.
You can delete this message when (if) the structure is changed. Hope this helps.
Thanks for the help, Hap. I’ll leave your comment up, as a prompt – If anyone else sees mistakes, do comment them up. Copying these structures atom-for-atom from the literature can be tricky at 1am!
Your Chemistry is very good..but why you didn’t synthesise the
Dictyo A
with regards,
Gobi