Total syntheses of 9-epoxyfalcarindiol and its diastereomer

Asymmetric Synthesis of Three Alkenyl Epoxides: Crafting the Sex Pheromones of the Elm Spanworm and the Painted Apple Moth

“…The next process was the crucial step in this transformation, which introduced chiral epoxy alcohol to primary allylic alcohol 11 via asymmetric Sharpless epoxidation. The synthesis of ((2S,3R)-3-nonyloxiran-2-yl) methanol (14) was accomplished (82% yield, 88% ee), catalyzed by L-(+)-diisopropyltartrate and Ti(OiPr)4 [19,20]. After one recrystallization using petroleum ether, the ee value of 14 increased to over 99%, which was determined via the 1 H NMR analysis of the Mosher ester of 14 [20,21].…”

“…The synthesis of ((2S,3R)-3-nonyloxiran-2-yl) methanol (14) was accomplished (82% yield, 88% ee), catalyzed by L-(+)-diisopropyltartrate and Ti(OiPr)4 [19,20]. After one recrystallization using petroleum ether, the ee value of 14 increased to over 99%, which was determined via the 1 H NMR analysis of the Mosher ester of 14 [20,21]. Similarly, using primary bromides 5 and 6 as starting materials, respectively, desired chiral blocks 15 and 16 could be obtained through the above-mentioned synthesis process of 14.…”