Total Synthesis of a Monomeric Phloroglucinol Derivative Isolated from Myrtus Communis

The first total synthesis of a monomeric phloroglucinol [(1R*,2S*)-2-hydroxy-2-isobuty1-4,4,6,6-tetramethyl-3,5-dioxocyclohexyl acetate] was achieved by stereoselective reduction of a symmetrical alpha-ketol as a key step. The corresponding cis-stereoisomer of the natural product was synthesized from phloroglucinol via cis-dihydroxylation using OsO4. Comparison of (HNMR)-H-1 data for synthetic 1 and 2 confirmed the trans-stereochemistry of the natural product.