Synthesis and reactivity of a putative biogenetic precursor to tricholomenyns B, C, D and E

A chemoenzymatic synthesis of the putative biogenetic precursor, 6, to the epoxy-quinol type natural products, tricholomenyns B, C, D and E (2–5, respectively), has been achieved. However, treatment of compound 6 under a variety of conditions failed to effect its conversion into any of the natural products 2–5. In contrast, the simple model system 22 reacts with acetic acid in the presence of stoichiometric quantities of Ti(OPr-i)4 to give the diacetate 23.