Synthesis and fungicidal activity of methylsulfanylmethyl ether derivatives of levoglucosenone

Sustainable One-Pot Synthesis and Polycondensation of a Levoglucosenone-Derived Cyclic Acetal Diol

“…Recently, Sharipov and co-workers 18 proposed the one-pot synthesis of HO-LGOL where they used 50 mol % of Et 3 N to catalyze LGO hydration and, after 2 h of reaction, added 1 equivalent of sodium borohydride to reduce the ketone (Scheme 6).…”

“…Recently, this reduction was optimized by Valeev and co-workers, who not only increased the yield to 90% but also partially greened the process by replacing methanol with water. 18 In a second report, they implemented a chemo-enzymatic pathway involving baker's yeast in an aqueous D-glucose solution. 19 Even though this strategy lowered the yield significantly to 39%, it offers a promising and greener alternative to NaBH 4 (Scheme 4).…”

Making natural products from renewable feedstocks: back to the roots?

“…[247][248][249][250] It is derived from levoglucosan (114), a product of the pyrolysis of cellulose. [251][252][253] Furthermore, it can be transformed to other useful compounds like (S)-g-hydroxymethyl-a,b-butenolide (HBO, 116) via Baeyer-Villiger oxidation, 254,255 the respective saturated derivative (2H-HBO, 118), 255 and D-(+)-ribono-1,4-lactone (117). 256 Although glucose is an important compound obtainable from cellulose that has elaborately been used for the natural product synthesis, those syntheses are only cursory covered in this review due to the wealth of literature already available.…”

(S)-γ-Hydroxymethyl-α,β-butenolide, a Valuable Chiral Synthon: Syntheses, Reactivity, and Applications

“…Recent work by Sharipov et al demonstrated that HBO can be efficiently converted into methylsulfanyl- HBO ( 173 ) (Scheme ). This molecule exhibits high fungicidal activity against Bipolaris sorokiniana, a crop parasite.…”