We present our efforts towards the total synthesis of Obtusallene V and VI. These compounds were isolated in 2000 from Laurencia obtuse along with several other related metabolites of this natural product family. Possessing complex functionality including a 5,5-oxaspiro core, a macrocyclic ether, and an unusual brominated allene, these compounds have precluded any total synthesis to date. We will utilize our newly developed halo-spirolactonization methodology to furnish the 5,5-oxaspiro core in a diastereo- and enantioselective manner via Bronsted basic catalysis. The conclusion of the synthesis is a simultaneous macrocyclic ether bromo-allene formation, which represents a possible biomimetic approach owing to the co-isolation of several eneyne metabolites with Obtusallene VI from Laurencia obtuse and Laurencia microladia. Our progress to date will be presented.

Towards the total synthesis of obtusallene V and VI

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