Clavilactones
A, B, and D are epidermal growth factor receptor
tyrosine kinase inhibitors that were isolated from cultures of the
fungus <i>Clitocybe clavipes</i>. Here, we report full details
of the total synthesis of these clavilactones. A key feature of our
synthetic approach is a ring-opening/ring-closing metathesis strategy
that allows the concise transformation of a cyclobutenecarboxylate
into a γ-butenolide. Coupled with enantioselective Ti/BINOL-catalyzed
alkynylation of a multisubstituted benzaldehyde and ring-closing metathesis
of a diene-bearing silylene acetal to construct the 10-membered carbocycle,
this strategy enabled the total synthesis of the natural enantiomers
(+)-clavilactone A and (−)-clavilactone B. In addition, the
correct structure of clavilactone D was determined by the synthesis
of two newly proposed structures. This research resulted in the asymmetric
synthesis of the revised (+)-clavilactone D
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