Furylcarbinol acetate

The reversal of the well-known transformation of sugars into pyrans has been detailed as a method for assembling simple monosaccharides from simple furans (71T1973). A compound of the 2-furylcarbinol type was converted by the Br2/MeOH procedure into a mixture of the cis and trans isomers of the corresponding 2,5-dimethoxy-2,5-dihydrofuran derivative (129). Mild acid hydrolysis of (129) resulted in cleavage of the acetal bonds with formation of the dicarbonyl compound (130) which underwent immediate cyclization to 2,3-dideoxy-DL-alk-2-enopyranos-4-ulose (131 Scheme 29). 

Acetylation. A comparative student experiment with salicylic acid and acetic anhydride demonstrates that common acetylation catalysts fall into the following order of relative effectiveness coned. H2SO4 > boron trifluoride etherate > pyridine > sodium acetate. Although it is a relatively weak catalyst, sodium acetate is completely nondestructive and can be employed in much larger than truly catalytic amounts. An example is the acetylation of furylcarbinol. A mixture of the reactants and solvent benzene was heated on the steam bath with stirring to prevent caking... 

The antibiotic phomalactone (50) has been obtained from a Drechslera species (62) and the fungus Hirsutella thompsonii var. synnematosa (63) and found to be active against a wide range of microorganisms. Phomalactone acetate (51) has been synthesized from 2-furylcarbinols (64, 65). The absolute stereochemistry of (+)-asperlin... 

---