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

Abstract

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. Show more