Synthesis of Natural Uvidin C

Abstract

The first synthesis of (−)-Uvidin C from (−)-drimenol through the ketol is described.

Drimenol: A Versatile Synthon for Compounds with trans-Drimane Skeleton

“…Wada and co-workers had isolated 62 from Aspergillus oryzae [34] and its structure was assigned on the basis of a racemic total synthesis [35]. Chiral ketone 33, obtained previously by Cortes et al [24], from (-)-drimenol, allowed the establishment of the absolute configuration of 62, by comparison of the specific rotation of the synthetic and natural sesquiterpene (Figure 23).…”

“…The first synthesis of (-)-uvidin C isolated from Lactarius uvidis Fries, from (-)-drimenol was described by Cortes et al [24]. According to a previous described procedure [25], acetylation and dihydroxylation of (-)-drimenol led to diol 30b, with an overall yield of 56%.…”

“…Finally, deprotection of 52, afforded (-)-polygodial in 30% overall yield (Figure19). Cortes et al [30] reported the synthesis of (-)ugandensidial, from diol 37, which in turn was prepared from (-)-drimenol [24]. Acetylation of 37 gave diacetate 58, in 75 % yield.…”

“…Cortes et al [24], from (-)-drimenol, allowed the establishment of the absolute configuration of 62, by comparison of the specific rotation of the synthetic and natural sesquiterpene ( Figure 23).…”

Synthesis of Drimanes from (+)-Larixol

“…These drimanes have generated considerable interest because of their potent antifeedant and molluscicidal activities. [10][11][12] Moreover, (-)-uvidin C (4) [13][14][15][16][17] and (-)-epi-albrassitriol (5), 18 which exhibits weak antiviral activity in in vitro tests against influenza A-and myxovirus (MIC 44.4 mg/mL; dosis tolerata maxima 133.3 mg/mL) were prepared (Figure 1).…”