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Totally Synthetic by Paul H. Docherty, 25 May 2006

Total Synthesis of Dictyodendrin B, C, E


A. Fürstner, M. M. Domostoj, B. Scheiper, J. Am. Chem. Soc. 2006, 128, 8087-8094.

DOI: 10.1021/ja0617800

Feeling a little rusty with your heterocyclic chemistry? The Fürstner group at the MPI Mülheim seem to know theirs pretty good, with total 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 6π 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 is definitely worth a read!