Deacylation reactions of 20-acetyl dinorcholanic lactones and 20,23-diacetyl furost-22-enes

Steroids

Volumn 75, Issue 3, 2010, Pages 240-244

  Hernández Linares, Ma Guadalupe ^a   Sandoval Ramírez, Jesús ^b   Meza Reyes, Socorro ^b   Montiel Smith, Sara ^b   Fernández Herrera, María A ^b   Bernès, Sylvain ^c  

^a Universidad del Istmo   (Mexico)

^b BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^c UNIVERSIDAD AUTÓNOMA DE NUEVO LEÓN   (Mexico)

Author keywords

20 Acetyl dinorcholanic lactones; Deacylation; Hydrazine hydrate; Microwaves; Sapogenins

Indexed keywords

ACETIC ACID DERIVATIVE; DIOSGENIN; HECOGENIN; HYDRAZINE; LACTONE DERIVATIVE; SARSASAPOGENIN;

ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DEACYLATION; DIASTEREOISOMER; ELIMINATION REACTION; MICROWAVE IRRADIATION; SCALE UP; STEROIDOGENESIS; X RAY CRYSTALLOGRAPHY;

EID: 76549124706     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2009.12.008     Document Type: Article

References (21)

1. Dewick P.M. Medicinal natural products. A biosynthetic approach. 2nd ed. (2002), John Wiley & Sons, Chichester p. 232-41
2. Tsuda K., Hayatsu R., Kishida Y., and Akagi S. Steroid studies. VI. Studies on the constitution of sargasterol. J Am Chem Soc 80 (1958) 921-925
3. Gonzalez A.G., Freire R., Francisco C.G., Salazar J.A., and Suarez E. New sources of steroid sapogenins. XIX. 20S-Hydroxyvespertilin, a new steroid lactone from Solanum vespertilio. Tetrahedron 29 (1973) 1731-1734
4. Idler D.R., Khalil M.W., Gilbert J.D., and Brooks C.J.W. Sterols of scallop. Part II. Structure of unknown sterols by combination gas-liquid chromatography and mass spectrometry. Steroids 27 (1976) 155-166
5. Vanderah D.J., and Djerassi C. Minor and trace sterols in marine invertebrate. Part 3. Novel marine sterols with modified bile acid side chain from the sea pen Ptilosarcus gurneyi. Tetrahedron Lett 18 (1977) 683-686
6. Jarzebski A. 20-Isosterols from the marine bivalve Macoma balthica. Steroids 55 (1990) 256-258
7. Tobari A., Teshima M., Koyanagi J., Kawase M., Miyamae H., Yoza K., et al. Spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides. Eur J Med Chem 35 (2000) 511-527
8. Quan H.J., Koyanagi J., Ohmori K., Uesato S., Tsuchido T., and Saito S. Preparations of heterospirostanols and their pharmacological activities. Eur J Med Chem 37 (2002) 659-669
9. Zmijewski M.A., Li W., Zjawiony J.K., Sweatman T.W., Chen J., Miller D.D., et al. Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3β,17α,20-triol and their bioactivity in melanoma cells. Steroids 74 (2009) 218-228
10. See for example:. Corcoran J.W., and Hirschmann H. The 20-epimer of the C22-lactone from tigogenin. J Am Chem Soc 78 (1956) 2325-2330
11. Hernandez-Linares G., Meza-Reyes S., Montiel-Smith S., Sandoval-Ramírez J., Gomez-Calvario V., and Bernes S. Synthesis and absolute configuration of (20R)-20-acetyl-23,24-bisnorcholanic lactones prepared from (E)-(20S,25R)- and (E)-(20S,25S)-20,23-diacetylfurost-22-enes. J Mex Chem Soc 51 (2007) 217-221 and references cited therein
12. Bondi A. van der Waals volumes and radii. J Phys Chem 68 (1964) 441-451
13. Tanabe M., and Hayashi K. Stereocontrolled synthesis of sterol side chains. J Am Chem Soc 102 (1980) 862-863
14. Marino J.P., and Abe H. New stereospecific approach to steroid side chains: conversion of dehydroepiandrosterone to cholesterol, isocholesterol, and their 15beta-hydroxy derivatives. J Am Chem Soc 103 (1981) 2907-2909
15. Mikami K., Kawamoto K., and Nakai T. A new Claisen approach to the stereospecific introduction of a steroids side chain at C-20. A simple synthesis of 20-epicholesterol via the β-face rearrangement. Chem Lett (1985) 115-118
16. Bruttomesso A.C., Doller D., and Gros E.G. Stereospecific synthesis of steroidal 20,16-γ-carbolactones. Synth Commun 28 (1998) 4043-4057
17. Tian W.S., Guan H.P., and Pan X.F. Lewis acid mediated ring F opening-acetylation of steroidal sapogenin. Chin Chem Lett 5 (1994) 1013-1016
18. Iglesias-Arteaga M.A., Jastrzebska I., and Morzycki J.W. Reactions of sapogenins with m-chloroperoxybenzoic acid catalyzed by Lewis acids. Polish J Chem 80 (2006) 667-671
19. XSCANS and XPREP. Madison, WI, USA: Siemens Analytical X-ray Instruments Inc.; 1996.
20. Sheldrick G.M. A short history of SHELX. Acta Crystallogr A64 (2008) 112-122
21. Bandhoria P., Gupta V.K., and Gupta D.K. Crystal structure of (25R)-spirost-5-en-3β-acetate. X-ray Struct Anal Online 22 (2006) x91-x92