Early Studies on the Synthesis of Agelastatin

SCHEME 5. A first generation approach to the agelastatin A skeleton through alkynyliodonium salt chemistry. 

These encouraging results prompted us to study the bicyclization chemistry of a more realistic model system in order to probe stereochemical issues relevant to the planned 32 - 31 conversion. Once again, we had no precedents to guide our expectations at this formative 

The conclusion that this synthesis plan was no longer tenable, seemed inescapable. And so, wiser but no further along, we decided to salvage what we could from this exercise and export that information into a second-generation approach to agelastatin A that was designed to avoid this stereochemical pitfall. 

SCHEME 9. Another failed attempt to access the agelastatin A skeleton via alkynyliodonium salt chemistry. 

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