Artículo

La versión final de este artículo es de uso interno. El editor solo permite incluir en el repositorio el artículo en su versión post-print. Por favor, si usted la posee enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

The particular behavior of 5β,6β steroidal epoxides carrying different groups at C-3 was studied. These epoxides may exhibit different cleavage behavior according to the nature of the solvent, the acid-base state of the medium, and the leaving abilities of the C-3 substituent. Results and alternative mechanisms are presented. © 1995.

Registro:

Documento: Artículo
Título:Cleavage reaction of 5β,6β steroidal epoxides carrying different groups at C-3
Autor:Gros, E.G.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Buenos Aires, Argentina
Palabras clave:cleavage of epoxides; ring A steroidal elimination; steroidal epoxides; epoxide; lithium chloride; n,n dimethylacetamide; steroid; article; chemical reaction; degradation; ph; proton nuclear magnetic resonance; Cations; Epoxy Compounds; Lithium; Molecular Structure; Solvents; Steroids; Support, Non-U.S. Gov't
Año:1995
Volumen:60
Número:7
Página de inicio:434
Página de fin:438
DOI: http://dx.doi.org/10.1016/0039-128X(95)00032-L
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:Cations; Epoxy Compounds; Lithium, 7439-93-2; Solvents; Steroids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v60_n7_p434_Gros

Referencias:

  • Chambers, Denny, Evans, Jones, Kasal, Meakins, Jones, Pragnell, Microbial hydroxylation of steroids Part VIII The pattern of monohydroxylation of diketones and ketoalcohols derived from 5α-androstane with cultures of the fungus Rhizopus nigricans (1973) Journal of the Chemical Society, Perkin Transactions 1, pp. 1500-1511
  • Riccio, Dini, Minale, Pizza, Zollo, Sevenet, Starfish saponins VII. Structure of luconicozide, a further steroidal cyclic glycoside from the pacific starfish Echanister luzonicus (1982) Experientia, 38, pp. 68-70
  • Takatsuto, Yazawa, Ikekawa, Morishita, Abe, Synthesis of (24-R)-28-homobrassinolide analogues and structure-activity relationships of brassinosteroids in the rice lamina inclination test (1983) Phytochemistry, 22, pp. 1393-1397
  • Lafont, Horn, (1989) Ecdysone, , J Koolman, G. Thieme-Verlag, Stuttgart and New York
  • Veleiro, Oberti, Burton, A ring D-aromatic with-anolide from Salpichroa origanifolia (1992) Phytochemistry, 31, pp. 935-937
  • Galagovsky, Burton, Gros, Z Naturforsch (1989) 5β6β Epoxidation of 3β-cholesteryl acetate and its analogues, 44 b, pp. 806-810
  • Galagovsky, Gros, Stereoselective epoxidation of stigmasterol and pregnenolone to give 5β,6β epoxides (1990) J Chem Res, pp. 366-367
  • Syamala, Das, Baskaran, Chandrasekaran, A novel and highly β selective epoxidation of Δ5-unsaturated steroids with permanganate ion (1992) J Am Chem Soc, 57, pp. 1288-1933
  • Oediger, Möller, Eiter, Byciclic amidines as reagents in organic syntheses (1972) Synthesis, pp. 591-598
  • Wolff, Huecas, Agosta, Convenient preparation of 1,1-disubstituted olefins from primary tosylates and iodides (1982) J Org Chem, 47, pp. 4358-4359
  • Traynham, Stone, Couvillion, A convenient synthesis of cis- and trans-cyclodecene (1967) J Org Chem, 32, pp. 510-511
  • Brown, Moritani, A new technique for controlling the direction of elimination reactions (1953) J Am Chem Soc, 75, pp. 4112-4113
  • Takatsuto, Kobayashi, Watanabe, Kuriyama, Furuse, (22E24S)-5α-Stigmasta-322-dien-6-one an intermediate of the isomerization of (22E24S)-3α5-cyclo-5α-stigmast-22-en-6-one into (22E24S)-5α-stigmasta-222-dien-6-one (1988) Agricultural and Biological Chemistry, 52, pp. 3217-3218
  • Mitra, Kapoor, Formation of Δ4-6-keto isomer in the synthesis of Δ2-6-keto steroids used as intermediates in the synthesis of brassinolide and analogous plant growth stimulators (1985) Synthetic Communications, 15, pp. 1087-1094
  • Zhou, The synthesis of brassinosteroids (1989) Pure and Applied Chemistry, 61, pp. 431-434
  • Morrison, Wilkinson, Neighbouring group participation in the cleavage of some steroidal hydroxy epoxides (1990) Journal of the Chemical Society, Perkin Transactions 1, pp. 345-351
  • Akagi, Tsuda, Steroid studies XXIII Dehydrobromination of 7-bromostigmasteryl benzoate (1961) CHEMICAL & PHARMACEUTICAL BULLETIN, 9, pp. 459-463
  • Weiss, Snyder, Conversion of some bicycloheptanols into chlorides using triphenylphosphine-carbon tetrachloride (1970) Stereochemistry and mechanistic implications, 35, pp. 1627-1632. , J Org Chem
  • Blunt, Hartshorn, Kirk, Reactions of epoxides. XVII. “Backbone rearrangements” of cholest-5-ene and 5,6α-epoxy-5α-cholestane (1969) Tetrahedron, 25, pp. 149-153
  • Blackett, Coxon, Hartshorn, Richards, Reactions of epoxides-XXIV (1969) The BF3-catalysed rearrangement of 4,5- and 5,6-epoxycholestanes, 25, pp. 4999-5005. , Tetrahedron
  • Morrison, Wilkinson, Cleavage reactions of some steroidal epoxides (1975) Tetrahedron Letters, pp. 2713-2716
  • Holland, Jahangir, Reactions of steroidal 45 and 56 epoxides with strong bases (1983) Canadian Journal of Chemistry, 61, pp. 2165-2170
  • Holland, Khan, Reaction of steroidal 56-epoxides and cyclohexene oxide with aluminium alkoxides (1985) Canadian Journal of Chemistry, 63, pp. 2763-2768
  • Williams, Maruyama, Synthesis of functionalized bicyclic dioxopiperazines via intramolecular epoxide opening (1987) J Org Chem, 52, pp. 4044-4047
  • Beard, Introduction of double bonds into the steroid system (1972) Organic Reaction in Steroid Chemistry, 1, pp. 265-374. , Eighth edition, J Fried, JH Edwards, Van Nostrand Reinhold, New York
  • Aburatani, Takeuchi, Mori, A simple synthesis of steroidal 3α5-cyclo-6-ones and their efficient transformation to steroidal 2-en-6-ones (1987) Synthesis, pp. 181-183
  • Fung, Siddall, Stereoselective synthesis of brassinolide: a plant growth promoting steroidal lactone (1980) J Am Chem Soc, 102, pp. 6580-6581
  • Berkoz, Cross, Adame, Carpio, Bowers, Steroids CCXXI Syntheses of some steroid dienes (1963) The Journal of Organic Chemistry, 28, pp. 1976-1982
  • Maskill, Catalysis (1985) The Physical Basis of Organic Chemistry, pp. 315-365. , Oxford University Press, Oxford, New York
  • Blunt, Stothers, 13C n.m.r. spectra of steroids (1977) A survey and commentary, 9, pp. 439-464. , Org Magn Res
  • Bhacca, Williams, (1964) Application of NMR spectroscopy in organic chemistry, Illustrations from the steroidal field, , Holden-Day, Inc, San Francisco, London, Amsterdam
  • Marchon, Rammaseul, Convenient synthesis of 5β,6β epoxides of some cholesteryl esters and Δ5-ketosteroids derivatives by catalytic β-stereoselective epoxidation (1989) Synthesis, p. 389

Citas:

---------- APA ----------
(1995) . Cleavage reaction of 5β,6β steroidal epoxides carrying different groups at C-3. Steroids, 60(7), 434-438.
http://dx.doi.org/10.1016/0039-128X(95)00032-L
---------- CHICAGO ----------
Gros, E.G. "Cleavage reaction of 5β,6β steroidal epoxides carrying different groups at C-3" . Steroids 60, no. 7 (1995) : 434-438.
http://dx.doi.org/10.1016/0039-128X(95)00032-L
---------- MLA ----------
Gros, E.G. "Cleavage reaction of 5β,6β steroidal epoxides carrying different groups at C-3" . Steroids, vol. 60, no. 7, 1995, pp. 434-438.
http://dx.doi.org/10.1016/0039-128X(95)00032-L
---------- VANCOUVER ----------
Gros, E.G. Cleavage reaction of 5β,6β steroidal epoxides carrying different groups at C-3. Steroids. 1995;60(7):434-438.
http://dx.doi.org/10.1016/0039-128X(95)00032-L