Stereoselective\nTotal Synthesis of Rhodocoranes I\nand J

We\nreport the stereoselective total synthesis of rhodocoranes I\nand J in 10 steps and 16.4% overall yield from (<i>S</i>)-limonene. The synthesis was accomplished through the convergent\nassembly of a highly substituted chiral cyclopentanone and a lithiated\nfuranyl silyl ketene acetal. The requisite cyclopentanone framework\nwas strategically constructed from the chiral pool, (<i>S</i>)-limonene, through a sequence of steps that included a hydroboration/oxidation,\nozonolysis, aldol condensation, reduction, and palladium-catalyzed\ndiastereoselective allylic transposition. This study provides a general\napproach to the synthesis of the rhodocorane family, known for their\nantibacterial, antifungal, and cytotoxic properties.