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Dictyodendrin B, C, and E   

25 May 2006 4,954 views 3 Comments

Dictyodendrin.jpg
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:

Dictyodendrin_1.jpg.jpg
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.

Dictyodendrin_2.jpg

Also containing an impressive benzylic Suzuki coupling and subsequent oxidation, this paper’s definately worth a read!

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3 Comments

  • Hap says:

    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.

  • Tot. Syn. says:

    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!

  • Gobi Rajeshwaran says:

    Your Chemistry is very good..but why you didn’t synthesise the
    Dictyo A
    with regards,
    Gobi