R. Sawa et al., ALDECALMYCIN, A NEW ANTIMICROBIAL ANTIBIOTIC FROM STREPTOMYCES .3. DETERMINATION OF ABSOLUTE-CONFIGURATION, Journal of antibiotics, 47(11), 1994, pp. 1280-1283
The planar structure of aldecalmycin (1) had been determined in the pr
evious paper, together with the conformations of the substituted Irans
decalin ring having one double bond and the sugar; beta-glucopyranosi
de type. The absolute configuration of 1 was a following problem to be
solved. X-Ray crystallographic analysis of crystalline 4',6'-O-benzyl
idenedihydroaldecalmycin (4) revealed the relative configuration. On t
he other hand, the stereoisomerism of the sugar was determined to be D
by the optical rotation value of tetra-O-acetyl-alpha-methylglucopyra
noside derived from 1. These results established the absolute configur
ation of 1.