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Volumn 8, Issue 2, 2004, Pages 219-228

Industrial synthesis of 4-chloro, 11β-arylestradiol: How to circumvent a poor diastereoselectivity

Author keywords

[No Author keywords available]

Indexed keywords

11BETA ARYL 17ALPHA METHYLESTRADIOL; 4 CHLORO 11BETA ARYLESTRADIOL; COPPER DERIVATIVE; EPOXIDE; ESTRADIOL DERIVATIVE; ESTRONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

EID: 1842558917     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0341622     Document Type: Article
Times cited : (11)

References (72)
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    • (b) For a monograph, see: Van Look, G.; Simchen, G.; Heberle, J. Silylating Agents; Fluka Chemica, Fluka Chemie AG: Buchs, Switzerland, 1995.
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  • 23
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    • note
    • LDA was prepared in situ from n-butyllithium and diisopropylamine in THF at 0°C.
  • 25
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    • see ref 6e
    • This type of dienone has already been described: see ref 6e.
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    • Joly, R.; Joly, J. (Roussel Uclaf.). FR 81840, 1962
    • (a) Joly, R.; Joly, J. (Roussel Uclaf.). FR 81840, 1962.
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    • note
    • The intermediates bearing a 17-hydroxyl group were less crystalline.
  • 62
    • 1842489650 scopus 로고    scopus 로고
    • note
    • The hydrochloride salt of the trisubstituted amine on the side chain was not acidic enough to catalyze the reaction.
  • 63
    • 0003514816 scopus 로고
    • Wiley Interscience and John Wiley & Sons: New York
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    • (1967) Reagents for Organic Synthesis
    • Fieser, M.1    Fieser, L.2
  • 64
    • 1842488921 scopus 로고    scopus 로고
    • (a) Fieser, M.; Fieser, L. Reagents for Organic Synthesis; Wiley Interscience and John Wiley & Sons: New York, 1967; Vol. 1, p 72; Vol. 2, p 38; Vol. 6, p 102.
    • Reagents for Organic Synthesis , vol.1 , pp. 72
  • 65
    • 1842489655 scopus 로고    scopus 로고
    • (a) Fieser, M.; Fieser, L. Reagents for Organic Synthesis; Wiley Interscience and John Wiley & Sons: New York, 1967; Vol. 1, p 72; Vol. 2, p 38; Vol. 6, p 102.
    • Reagents for Organic Synthesis , vol.2 , pp. 38
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    • (a) Fieser, M.; Fieser, L. Reagents for Organic Synthesis; Wiley Interscience and John Wiley & Sons: New York, 1967; Vol. 1, p 72; Vol. 2, p 38; Vol. 6, p 102.
    • Reagents for Organic Synthesis , vol.6 , pp. 102
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    • note
    • As bromination of arylestrone hydrochloride 14 using N-bromosuccinimide (NBS, 1.5 equiv) and HCl (0.5 equiv) resulted in a very slow reaction, NBS is probably not the actual brominating agent in the presence of NCS.
  • 70
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    • note
    • 1.
  • 71
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    • note
    • F. Nique, and J. L. Borgna et al. isolated a deconjugated dienone such as 9c after alkaline treatment of an aromatisation mixture (ref 13d). This dienone was probably the saponification product of a trienol acetate similar to 13c.
  • 72
    • 1842489660 scopus 로고    scopus 로고
    • note
    • Using hexachloroacetone as the epoxidation catalyst, the yield in crystallised 4a was 43%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.