Abstract
Various novel carbocyclization processes were observed to occur in Lewis acid mediated cyclizations of an allylic epoxide substrate with a tethered enol(ate) function as nucleophile. Both cation-olefin polycyclization pathways and S N-prime macrocyclization processes were observed to occur in the presence of different Lewis acid additives. Lewis acid additives were also observed to direct the stereochemistry of allylic epoxide opening by S N-prime addition of halide ions. This provided a route to the corresponding E- or Z-allylic halides, which served as substrates in an alternative, successful approach to the terpestacin/fusaproliferin ring system by a subsequent alkylative macrocyclization reaction.
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