We present here a novel approach to the enantioselective total synthesis of poitediene, a metabolite of red algae possessing a unique “<i>in-out</i>” bridged cyclic structure. We envision that the highly strained 12-membered macrocyclic ether is constructed by etherification using a thiocarbenium ion intermediate. The oxolane core was built from epoxy alcohol by zinc-catalyzed etherification, which took place via stereospecific cycloisomerization. Described in this poster are the details of our synthetic route that provides efficient access to the highly functionalized 2,12- dioxabicyclo[9.2.1]tetradecane system.

Studies toward the total synthesis of poitediene

256th National Meeting (2018)

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