Enantioselective synthesis of antibiotic (+)-rancinamycin III derivative and two protected carbasugars of the α-D-talo-series from furan

Article abstract of DOI:10.1016/S0957-4166(99)00358-4

The synthesis of (+)-1, a carbasugar related to rancinamycin III, has been achieved from diene (+)-3 in two steps using as the key step the transformation of alkyne (-)-2, obtained by resolution of alcohol 6, into diene (+)-3 by treatment with Na/MeOH. Moreover, reduction of the carbonyl group in (+)-1 affords diol (+)-19, in which different protection strategies of the hydroxy groups allows one to obtain, selectively, protected derivatives of α-D-carbatalopyranose (+)-4a and its 6-desoxy derivative (+)- 4b to be obtained selectively.