Application of the Nickel-Mediated Neopentyl Coupling in the Total Synthesis of the Marine Natural Product Arenarol

초록

Racemic arenarol (1) has been synthesized from the known decalin 5 beta-carbethoxy-1,1-(1,2-ethylenedioxy)-5 alpha,8a beta-dimethyl-1,2,3,5,6,7,8,8a-octahydro-6-oxonaphthalene (9) via a short, efficient, and highly stereocontrolled sequence. Key steps in this synthesis are the directed hydrogenation of an unsaturated neopentyl alcohol to provide stereocontrolled formation of the two adjacent tertiary centers and subsequent elaboration of the arenarol skeleton via a nickel-mediated coupling of the corresponding neopentyl iodide. This sequence demonstrates the value of nickel-mediated cross-coupling reactions for carbon-carbon bond formation at neopentyl centers.

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