Abstract
The first synthesis of pennogenin, an aglycone of bioactive components of Chinese traditional medicine named “Chonglou”(Paris), starting from diosgenin, has been reported, which displays a new strategy of utilizing the resource compounds. According to this new strategy, the full and rational utilization of the intact skeleton and functional groups of starting material has been realized in the conversion of diosgenin to pennogenin. The key step for synthesis of pennogenin is the regioselective transformation of cholest-5-en-16,22-dion-3,26-diol to cholest-5,16-dien-22-on-3,26-diol, which can be used to synthesize other bioactive steroids such as cephalostatin and OSW-1.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Li, H., The Genus Paris (Trilliaceae), Beijing: Science Press, 1998.
Woo, E. R., Kim, J. M., Kim, H. J. et al., A cytotoxic pennogenin glycoside from majanthemum dilatatum, Planta. Med., 1998, 64: 466–468.
Guo, C. X., LaCour, T. G., Fuchs, P. L., On the relationship of OSW-1 to the cephalostatins, Bioorg. & Med. Chem. Lett., 1999, 9: 419–424.
Kubo, S., Mimaki, Y., Terao, M. et al., Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae, Phytochemistry, 1992, 31:3969–3973.
Breslow, R., Biomimetic chemistry and artifical enzymes: catalysis in design, Acc. Chem. Res., 1995, 28: 146–153.
Piatak, D. M., Wicha, J., Various approaches to the construction of aliphatic side chains of steroids and related compounds, Chem. Rev., 1978, 78: 199–241.
Redpath, J., Zeelen, F. J., Stereoselective synthesis of steroid side-chains, Chem. Soc. Rev., 1983, 25: 75–98.
Lee, E., Liu, Y. T., Solomon, P. H. et al., Stereospecific conversion of diosgenin to α-ecdysone, J. Am. Chem. Soc., 1976, 98: 1634–1635.
Betancor, C., Freire, R., Perez-Martin, I. et al., A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins, Org. Lett., 2002, 4: 1295–1297.
Yu, B, Liao, B., J. C., Zhang, J. B. et al., The first synthetic route to furostan saponins, Tetra. Lett., 2001, 42: 77–79.
Cheng, M. S., Wang, Q. L., Tian, Q. et al., Total synthesis of methyl protodioscin: a potent agent with antitumor activity, J. Org. Chem., 2003, 68: 3658–3662.
Bovicelli, P., Lupattelli, P., Fracassi, D. et al., Sapogenins and dimethyldioxirane, a new entry to cholestanes functionalized at the side chain, Tetra. Lett.,1994, 35: 935–938.
Arthur, F. K., Michael, L. M., Leslie, G. P., Synthesis of (20R, 25R)-cholest-5-ene-3,26-diol and the occurrence of base-catalyzed 1,5-hydride shift in a steroidal 1,5-ketol, J. Org. Chem., 1985, 50: 2359–2365.
Mahato, S. B., Sahu, N. P., Ganguly, A. N., Steroidal saponins from dioscorea floribunda: structures of floribundasaponins A and B, Phytochemistry, 1981, 20: 1943–1946.
Nohara, T., Miyahara, K., Kawasak, T., The structure of Pennogenin, Chem. Pharm. Bull., 1974, 22: 1772–1780.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Tian, W., Xu, Q., Chen, L. et al. Synthesis of pennogenin utilizing the intact skeleton of diosgenin. Sc. China Ser. B-Chem. 47, 142–144 (2004). https://doi.org/10.1360/03yb0002
Received:
Issue Date:
DOI: https://doi.org/10.1360/03yb0002