Stereoselective Total Synthesis of Rhodocoranes I and J
Cooper A Vincent1, Vaishnavi N Nair1, Uttam K Tambar1
1Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States.
Abstract:
We report the stereoselective total synthesis of rhodocoranes I and J in 10 steps and 16.4% overall yield from (S)-limonene. The synthesis was accomplished through the convergent assembly of a highly substituted chiral cyclopentanone and a lithiated furanyl silyl ketene acetal. The requisite cyclopentanone framework was strategically constructed from the chiral pool, (S)-limonene, through a sequence of steps that included a hydroboration/oxidation, ozonolysis, aldol condensation, reduction, and palladium-catalyzed diastereoselective allylic transposition. This study provides a general approach to the synthesis of the rhodocorane family, known for their antibacterial, antifungal, and cytotoxic properties.
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