10.1021/ol702655c
The study focused on the asymmetric synthesis of L-(+)-Noviose, a sugar component of the antibiotics novobiocin and coumarin. The goal of the study was to develop alternative and rapid methods to synthesize L-(+)-Noviose from readily available non-carbohydrate starting materials while taking advantage of stoichiometric and asymmetric processes. The researchers achieved this goal through two independent methods, one involving six steps with an overall yield of 27% and the other involving nine steps with an overall yield of 20%. A variety of chemicals were used in the synthesis, including 2,2-dimethyl-1,3-cyclopentanedione, (S)-B-Me-oxaborane ((S)-B-Me-CBS), BH3 N,N-dimethylbenzene complex (DEANB), methyl ethers, Sc(OTf)3, Saegusa oxidation, Pd(OAc)2, trimethylsilyl ketene intermediates, ene palladium, NaH, Grubbs second generation catalyst, DIBALH, water, and other chemicals for non-catalyzed xylene reactions. The study conclusions highlight the successful development of two efficient synthetic routes to L-(+)-Noviose, suitable for the synthesis of unnatural analogs, without the need for protecting groups, and utilizing commercially available reagents such as Corey's CBS and Brown's reagent.
