메뉴 건너뛰기




Volumn 69, Issue 1, 2004, Pages 35-42

Stereoselective reactions of (20R)-3,20-dihydroxy-(3′,4′- dihydro-2′H-pyranyl)-5-pregnene derivatives form 27-nor-3,20,23,26- tetrahydroxy-cholesten-22-ones and related bromo ketones

Author keywords

(20R,23R) 27 Nor 3,20,23,26 tetrahydroxy cholest 5 en 22 one 3 acetate; 23 Bromo (20R,23R) 27 nor 3,20,26 trihydroxy cholest 5 en 22 one; Steroids

Indexed keywords

23 BROMO 3,20,26 TRIHYDROXY 27 NORCHOLEST 5 EN 22 ONE; 3 CHLOROPERBENZOIC ACID; 3,20 DIHYDROXY(3',4' DIHYDRO 2'H PYRANYL) 5 PREGNENE; 3,20,23,26 TETRAHYDROXY 27 NORCHOLEST 5 EN 22 ON 3 ACETATE; 3,4 DIHYDRO 2H PYRAN; ACETIC ACID DERIVATIVE; CHOLESTANE DERIVATIVE; KETONE DERIVATIVE; METHANOL; PREGNANE DERIVATIVE; PREGNENOLONE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG; [6' (3',4' [2'H]DIHYDROPYRANYL)]PREGN 5 ENE 3BETA 20 DIOL 3 ACETATE;

EID: 0347989350     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2003.09.011     Document Type: Article
Times cited : (1)

References (25)
  • 1
    • 0014559339 scopus 로고
    • A preliminary report on the intermediates in the conversion in vitro of cholesterol to pregnenolone in adrenal preparations
    • Burstein S., Gut M. A preliminary report on the intermediates in the conversion in vitro of cholesterol to pregnenolone in adrenal preparations. Steroids. 14:1969;207-217.
    • (1969) Steroids , vol.14 , pp. 207-217
    • Burstein, S.1    Gut, M.2
  • 2
    • 0005717933 scopus 로고
    • 20α,22ξ-Dihydroxycholesterol, an intermediate in the biosynthesis of pregnenolone (3β-hydrodroxypregn-5-en-20-one) from cholesterol
    • Shimizu K., Gut M., Dorfman R.I. 20α,22ξ-Dihydroxycholesterol, an intermediate in the biosynthesis of pregnenolone (3β-hydrodroxypregn-5- en-20-one) from cholesterol. J. Biol. Chem. 237:1962;699-702.
    • (1962) J. Biol. Chem. , vol.237 , pp. 699-702
    • Shimizu, K.1    Gut, M.2    Dorfman, R.I.3
  • 3
    • 0014774991 scopus 로고
    • The synthesis and stereochemistry of (22R)-20α,22 and (22S)-20α,22-dihydroxycholesterol
    • Chaudhuri N.K., Nickolson R., Kimball H., Gut M. The synthesis and stereochemistry of (22R)-20α,22 and (22S)-20α,22- dihydroxycholesterol. Steroids. 15:1970;525-539.
    • (1970) Steroids , vol.15 , pp. 525-539
    • Chaudhuri, N.K.1    Nickolson, R.2    Kimball, H.3    Gut, M.4
  • 4
    • 0348202536 scopus 로고
    • Synthesis of rubrosterone, a metabolite of insect-molting substances from Achyranthes rubrofusca
    • Hikino H., Hikino Y., Takemoto T. Synthesis of rubrosterone, a metabolite of insect-molting substances from Achyranthes rubrofusca. Tetrahedron Lett. 40:1968;4255-4256.
    • (1968) Tetrahedron Lett. , vol.40 , pp. 4255-4256
    • Hikino, H.1    Hikino, Y.2    Takemoto, T.3
  • 5
    • 0014386149 scopus 로고
    • Steroids. II. Stimulatory effect of insect-metamorphosing steroids from Achyranthes and Cyathula on protein synthesis in mouse liver
    • Otaka T., Uchiyama M., Okui S., Takemoto T., Hikino H., Ogawa S.et al. Steroids. II. Stimulatory effect of insect-metamorphosing steroids from Achyranthes and Cyathula on protein synthesis in mouse liver. Chem. Pharm. Bull. 16:1968;2426-2429.
    • (1968) Chem. Pharm. Bull. , vol.16 , pp. 2426-2429
    • Otaka, T.1    Uchiyama, M.2    Okui, S.3    Takemoto, T.4    Hikino, H.5    Ogawa, S.6
  • 6
    • 0017048239 scopus 로고
    • Inokosterone, an insect methamorphosing substance from Achiranthes faurieri. Absolute configuration and synthesis
    • Hikino H., Mohri K., Hikino Y., Arihara S., Takemoto T., Mori H.et al. Inokosterone, an insect methamorphosing substance from Achiranthes faurieri. Absolute configuration and synthesis. Tetrahedron. 32:1976;3015-3021.
    • (1976) Tetrahedron , vol.32 , pp. 3015-3021
    • Hikino, H.1    Mohri, K.2    Hikino, Y.3    Arihara, S.4    Takemoto, T.5    Mori, H.6
  • 7
    • 0038188828 scopus 로고    scopus 로고
    • Identity of the moulting hormones of insects and crustaceans.
    • Horn DHS, Middleton EJ, Wunderlich JA. Identity of the moulting hormones of insects and crustaceans. Chem Commun 339-41.
    • Chem Commun , pp. 339-341
    • Dhs, H.1    Middleton, E.J.2    Wunderlich, J.A.3
  • 8
    • 0016682761 scopus 로고
    • Shidasterone, an insect metamorphosing substance from Blechnum niponicum: Structure
    • Hikino H., Okuyama T., Arihara S., Hikino Y., Takemoto T., Mori H.et al. Shidasterone, an insect metamorphosing substance from Blechnum niponicum: Structure. Chem. Pharm. Bull. 23:1975;1458-1479.
    • (1975) Chem. Pharm. Bull. , vol.23 , pp. 1458-1479
    • Hikino, H.1    Okuyama, T.2    Arihara, S.3    Hikino, Y.4    Takemoto, T.5    Mori, H.6
  • 9
    • 0347572814 scopus 로고
    • Studies on a steroidal plant-growth regulator. Part 26. Stereoselective construction of the brassinolide side-chain: New practical syntheses of brassinolide analogues from hyodeoxycholic acid.
    • Zhou W-S, Huang L-F, Sun L-Q, Pan X-F. Studies on a steroidal plant-growth regulator. Part 26. Stereoselective construction of the brassinolide side-chain: new practical syntheses of brassinolide analogues from hyodeoxycholic acid. J Chem Soc, Perkin Trans 1 1992;2039-43.
    • (1992) J Chem Soc, Perkin Trans 1 , pp. 2039-2043
    • Zhou, W.-S.1    Huang, L.-F.2    Sun, L.-Q.3    Pan, X.-F.4
  • 10
    • 0025820232 scopus 로고
    • A concise synthesis of the brassinolide side chain
    • Back T.G., Blazecka P.G., Krishna M.V. A concise synthesis of the brassinolide side chain. Tetrahedron Lett. 32:1991;4817-4818.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 4817-4818
    • Back, T.G.1    Blazecka, P.G.2    Krishna, M.V.3
  • 11
    • 37049077541 scopus 로고
    • Stereoselective synthesis of plant-growth-regulating steroids: Brassinolide, castasterone, and their 24,25-substituted analogues.
    • Tsubuki M, Keino K, Honda T. Stereoselective synthesis of plant-growth-regulating steroids: brassinolide, castasterone, and their 24,25-substituted analogues. J Chem Soc, Perkin Trans 1 1992;2643-9.
    • (1992) J Chem Soc, Perkin Trans 1 , pp. 2643-2649
    • Tsubuki, M.1    Keino, K.2    Honda, T.3
  • 13
    • 0023834961 scopus 로고
    • Interaction of a spin-labeled cholesterol derivative with the cytochrome P-450scc active site
    • Lange R., Maurin L., Larroque C., Bienvenue A. Interaction of a spin-labeled cholesterol derivative with the cytochrome P-450scc active site. Eur. J. Biochem. 172:1988;189-195.
    • (1988) Eur. J. Biochem. , vol.172 , pp. 189-195
    • Lange, R.1    Maurin, L.2    Larroque, C.3    Bienvenue, A.4
  • 14
    • 0020055403 scopus 로고
    • Metabolism of 27-nor-24,25-dihydrolanosterol and 23,24,25,26,27- pentanordihydrolanosterol by rat liver homogenate preparations
    • Sato Y., Sonoda Y. Metabolism of 27-nor-24,25-dihydrolanosterol and 23,24,25,26,27-pentanordihydrolanosterol by rat liver homogenate preparations. Chem. Pharm. Bull. 30:1982;628-634.
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 628-634
    • Sato, Y.1    Sonoda, Y.2
  • 15
    • 0025936641 scopus 로고
    • Novel synthesis of cholesterol analogues: Condensation of with pregnenolone dihydropyran or dihydrofuran
    • Szendi Zs., Sweet F. Novel synthesis of cholesterol analogues: condensation of with pregnenolone dihydropyran or dihydrofuran. Steroids. 56:1991;458-463.
    • (1991) Steroids , vol.56 , pp. 458-463
    • Szendi, Zs.1    Sweet, F.2
  • 16
    • 0347572815 scopus 로고
    • Synthesis of methyl 2,3-anhydro-4-deoxy-6-O-methyl-α-DL- lyxohexopyranoside
    • Sweet F., Brown R.K. Synthesis of methyl 2,3-anhydro-4-deoxy-6-O-methyl- α-DL-lyxohexopyranoside. Can. J. Chem. 46:1968;2283-2298.
    • (1968) Can. J. Chem. , vol.46 , pp. 2283-2298
    • Sweet, F.1    Brown, R.K.2
  • 17
    • 0001451148 scopus 로고    scopus 로고
    • Diastereoselectivity in epoxidation of substituted cyclohexenes by dimethyldioxirane
    • Murray R.W., Singh M., Williams B.L., Moncrtieff H.M. Diastereoselectivity in epoxidation of substituted cyclohexenes by dimethyldioxirane. J. Org. Chem. 61:1996;1830-1841.
    • (1996) J. Org. Chem. , vol.61 , pp. 1830-1841
    • Murray, R.W.1    Singh, M.2    Williams, B.L.3    Moncrtieff, H.M.4
  • 18
    • 37049138320 scopus 로고
    • Epoxidation of allylic alcohols with peroxy-acids. Attempts to define transition state geometry.
    • Chamberlain ML, Roberts Whitham GH. Epoxidation of allylic alcohols with peroxy-acids. Attempts to define transition state geometry. J Chem Soc (B) Phys. Org. 1970;1374-81.
    • (1970) J Chem Soc (B) Phys. Org. , pp. 1374-1381
    • Chamberlain, M.L.1    Roberts Whitham, G.H.2
  • 19
    • 0034670616 scopus 로고    scopus 로고
    • Substituent dependence of the diastereofacial selectivity in iodination and bromination of glycals related to cyclic enol ethers
    • Boschi A., Chiappe C., De Rubertis A., Ruasse M.F. Substituent dependence of the diastereofacial selectivity in iodination and bromination of glycals related to cyclic enol ethers. J. Org. Chem. 65:2000;8470-8477.
    • (2000) J. Org. Chem. , vol.65 , pp. 8470-8477
    • Boschi, A.1    Chiappe, C.2    De Rubertis, A.3    Ruasse, M.F.4
  • 20
    • 33947569274 scopus 로고
    • Studies in stereochemistry. X. the rule of "steric Control of Asymmetric Induction" in the syntheses of acyclic systems
    • Cram D.J., Abd Elhafez F.A. Studies in stereochemistry. X. The rule of "Steric Control of Asymmetric Induction" in the syntheses of acyclic systems. J. Am. Chem. Soc. 74:1952;5828-5835.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 5828-5835
    • Cram, D.J.1    Abd Elhafez, F.A.2
  • 21
    • 85030919405 scopus 로고    scopus 로고
    • Morrison JD, editor. New York: Academic Press; 1983 [chapter 5].
    • Eliel EL. In: Morrison JD, editor. Asymmetric synthesis, vol. 2. New York: Academic Press; 1983 [chapter 5].
    • Asymmetric Synthesis , vol.2
    • Eliel, E.L.1
  • 22
    • 49949128203 scopus 로고
    • Torsional strain involving partial bonds. the stereochemistry of the lithium aluminium hydride reduction of some simple open-chain ketones
    • Cherest M., Felkin H., Prudent N. Torsional strain involving partial bonds. The stereochemistry of the lithium aluminium hydride reduction of some simple open-chain ketones. Tetrahedron Lett. 9:1968;2199-2204.
    • (1968) Tetrahedron Lett. , vol.9 , pp. 2199-2204
    • Cherest, M.1    Felkin, H.2    Prudent, N.3
  • 23
    • 33845281063 scopus 로고
    • Electronic and conformational effects on .pi.-facial stereoselectivity in nucleophilic additions to carbonyl compounds
    • Wu Y.-D., Houk K.N. Electronic and conformational effects on .pi.-facial stereoselectivity in nucleophilic additions to carbonyl compounds. J. Am. Chem. Soc. 109:1987;908-910.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 908-910
    • Wu, Y.-D.1    Houk, K.N.2
  • 24
    • 0343651237 scopus 로고
    • Cis- and trans-2,4-dimethoxytetrahydropyrans. Models for study of the anomeric effect
    • Sweet F., Brown R.K. Cis- and trans-2,4-dimethoxytetrahydropyrans. Models for study of the anomeric effect. Can. J. Chem. 46:1968;1543-1594.
    • (1968) Can. J. Chem. , vol.46 , pp. 1543-1594
    • Sweet, F.1    Brown, R.K.2
  • 25
    • 0023333492 scopus 로고
    • Affinity labeling of hormone-specific proteins
    • Sweet F., Murdock G.M. Affinity labeling of hormone-specific proteins. Endocr. Rev. 8:1987;154-174.
    • (1987) Endocr. Rev. , vol.8 , pp. 154-174
    • Sweet, F.1    Murdock, G.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.