Total Synthesis of the Proposed Structure of Trichodermatide A

J. Org. Chem., 2014, 79 (20), pp 9812–9817, 2014, 79, 9812.9817 published on 28.08.2014
J. Org. Chem.
A short total synthesis of the published structure of racemic trichodermatide A is reported. Our synthesis involves a Knoevenagel condensation/Michael addition sequence, followed by the formation of tricyclic hexahydroxanthene-dione and a diastereoselective bis-hydroxylation. The final product, the structure of which was confirmed by X-ray crystallography, has NMR spectra that are very similar, but not identical, to those of the isolated natural product. Quantum chemically computed ¹³C shifts agree well with the present NMR measurements.
TU München