Abstract
The diastereodifferentiating reactions between a prochiral substrate and a reagent connected with optically active 2, 4-pentanediol were studied. The reactions based on this simple design were found to give products of over 99% diastereomeric excess during carbenoid addition, mata-arene-olefin photocycloaddition, oxidative couplings, and epoxidation, and after removal of the chiral auxiliary from the products, optically pure compounds were obtained in good yields. By using the obtained asymmetric reaction, total synthesis of (+) -africanol was achieved in 16 steps. Newly found highly effective and diastereodifferentiating radical abstraction was applied for total syntheses of (+) -ipomeamarone and (-) -ngaione.
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