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Practical synthesis of 16,22-diketocholesterol acetate, a precursor of anticancer saponin OSW-1, from diosgenin

Margarita Aleksandrovna Lapitskaya 1
Margarita Aleksandrovna Lapitskaya
, 
Ljudmila Leonidovna Vasiljeva 1
Ljudmila Leonidovna Vasiljeva
, 
Kazimir Konstantinovich Pivnitsky 1
Kazimir Konstantinovich Pivnitsky
10.1016/j.mencom.2010.11.005
Published 2010-11-02
Communication , Volume 20, Issue 6, 318-320
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Lapitskaya M. A., Vasiljeva L. L., Pivnitsky K. K. Practical synthesis of 16,22-diketocholesterol acetate, a precursor of anticancer saponin OSW-1, from diosgenin // Mendeleev Communications. 2010. Vol. 20. No. 6. pp. 318-320.
GOST all authors (up to 50) Copy
Lapitskaya M. A., Vasiljeva L. L., Pivnitsky K. K. Practical synthesis of 16,22-diketocholesterol acetate, a precursor of anticancer saponin OSW-1, from diosgenin // Mendeleev Communications. 2010. Vol. 20. No. 6. pp. 318-320.
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TY - JOUR
DO - 10.1016/j.mencom.2010.11.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.11.005
TI - Practical synthesis of 16,22-diketocholesterol acetate, a precursor of anticancer saponin OSW-1, from diosgenin
T2 - Mendeleev Communications
AU - Lapitskaya, Margarita Aleksandrovna
AU - Vasiljeva, Ljudmila Leonidovna
AU - Pivnitsky, Kazimir Konstantinovich
PY - 2010
DA - 2010/11/02
PB - Mendeleev Communications
SP - 318-320
IS - 6
VL - 20
ER -
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@article{2010_Lapitskaya,
author = {Margarita Aleksandrovna Lapitskaya and Ljudmila Leonidovna Vasiljeva and Kazimir Konstantinovich Pivnitsky},
title = {Practical synthesis of 16,22-diketocholesterol acetate, a precursor of anticancer saponin OSW-1, from diosgenin},
journal = {Mendeleev Communications},
year = {2010},
volume = {20},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.11.005},
number = {6},
pages = {318--320},
doi = {10.1016/j.mencom.2010.11.005}
}
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Lapitskaya, Margarita Aleksandrovna, et al. “Practical synthesis of 16,22-diketocholesterol acetate, a precursor of anticancer saponin OSW-1, from diosgenin.” Mendeleev Communications, vol. 20, no. 6, Nov. 2010, pp. 318-320. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.11.005.

Abstract

An improved method using dibromide protection of the 5,6-double bond has been developed for the synthesis of the title compound, which is a key intermediate in the synthesis of saponin OSW-1 from diosgenin.

References

1.
Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae
Kubo S., Mimaki Y., Terao M., Sashida Y., Nikaido T., Ohmoto T.
Phytochemistry, 1992
2.
Cholestane glycosides with potent cytostatic activities on various tumor cells from Ornithogalum saundersiae bulbs
Mimaki Y., Kuroda M., Kameyama A., Sashida Y., Hirano T., Oka K., Maekawa R., Wada T., Sugita K., Beutler J.A.
Bioorganic and Medicinal Chemistry Letters, 1997
3.
OSW-1: a Natural Compound With Potent Anticancer Activity and a Novel Mechanism of Action
Zhou Y., Garcia-Prieto C., Carney D.A., Xu R., Pelicano H., Kang Y., Yu W., Lou C., Kondo S., Liu J., Harris D.M., Estrov Z., Keating M.J., Jin Z., Huang P., et. al.
Journal of the National Cancer Institute, 2005
4.
First Total Synthesis of an Exceptionally Potent Antitumor Saponin, OSW-1
Deng S., Yu B., Lou Y., Hui Y.
Journal of Organic Chemistry, 1998
6.
Synthesis of OSW-1 analogues and a dimer and their antitumor activities
Ma X., Yu B., Hui Y., Miao Z., Ding J.
Bioorganic and Medicinal Chemistry Letters, 2001
7.
Y. Pan, Ph.D. Thesis, Case Western Reserve University, USA, 2005.
9.
Synthesis of 5(6)-dihydro-OSW-1 by using the intact skeleton of tigogenin
Chen L., Xu Q., Huang H., Lin J., Tian W.
Tetrahedron Letters, 2007
12.
Total Synthesis of the Anticancer Natural Product OSW-1
Yu W., Jin Z.
Journal of the American Chemical Society, 2002
13.
23-Oxa-Analogues of OSW-1: Efficient Synthesis and Extremely Potent Antitumor Activity
Shi B., Wu H., Yu B., Wu J.
Angewandte Chemie - International Edition, 2004
14.
Synthesis of OSW-1 analogs with modified side chains and their antitumor activities
Deng L., Wu H., Yu B., Jiang M., Wu J.
Bioorganic and Medicinal Chemistry Letters, 2004
15.
Synthesis of 5,6-Dihydro-OSW-1 and its antitumor activities
Deng L., Wu H., Yu B., Jiang M., Wu J.
Chinese Journal of Chemistry, 2010
16.
OSW Saponins:  Facile Synthesis toward a New Type of Structures with Potent Antitumor Activities
Shi B., Tang P., Hu X., Liu J.O., Yu B.
Journal of Organic Chemistry, 2005
17.
10.1016/j.mencom.2010.11.005_bib0030_8
Kruszewska
Pol. J. Chem., 2006
18.
Synthesis of OSW saponin analogs with modified sugar residues and their antiproliferative activities
Tang P., Mamdani F., Hu X., Liu J.O., Yu B.
Bioorganic and Medicinal Chemistry Letters, 2007
19.
New Analogues of the Potent Cytotoxic Saponin OSW-1
Wojtkielewicz A., Długosz M., Maj J., Morzycki J.W., Nowakowski M., Renkiewicz J., Strnad M., Swaczynová J., Wilczewska A.Z., Wójcik J.
Journal of Medicinal Chemistry, 2007
20.
A Total Synthesis of OSW-1
Xue J., Liu P., Pan Y., Guo Z.
Journal of Organic Chemistry, 2007
23.
Sterols. CLVII. Sapogenins. LXIX.1 Isolation and Structures of Thirteen New Steroidal Sapogenins. New Sources for Known Sapogenins
Marker R.E., Wagner R.B., Ulshafer P.R., Wittbecker E.L., Goldsmith D.P., Ruof C.H.
Journal of the American Chemical Society, 1943
25.
Steroids. LXXXI.1 Transformation of Sapogenins to Androgens and Estrogens. Beckmann Rearrangement of ▵16-20-Ketosteroids
ROSENKRANZ G., MANCERA O., SONDHEIMER F., DJERASSI C.
Journal of Organic Chemistry, 1956
28.
Reaction of the Steroidal Sapogenin Spiroketal System with Ethanedithiol1
DJERASSI C., HALPERN O., PETTIT G.R., THOMAS G.H.
Journal of Organic Chemistry, 1959
29.
R. Suhr, Ph.D. Thesis, Institute für Organische Chemie der Universität Hamburg, FRG, 2001.
31.
Stereoselective opening of ring E in furostan sapogenins. An efficient route to 16,22R,26-hydroxy steroids
González A.G., Francisco C.G., Freire R., Hernández R., Salazar J.A., Suárez E.
Tetrahedron Letters, 1974
32.
Rosado-Abon A., Romero-Avila M., Iglesias-Arteaga M.A.
Arkivoc, 2008
34.
Protective Groups in Organic Chemistry, ed. J. F. W. McOmie, Plenum Press, London–New York, 1973.
35.
L. F. Fieser and M. Fieser, Steroids, Reinhold Publishing Corporation, New York, 1959.
37.
Stereochemistry of the Cholesterol Dibromides1
Barton D.H., Miller E.
Journal of the American Chemical Society, 1950