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Volumn , Issue 2, 2006, Pages 312-314

Desymmetrization of the anti-meso-acetylmethyldivinylcyclopentane by directed epoxidation and its application to the synthesis of a polyfunctionalized trans-hydrindane unit

Author keywords

Desymmetrization; Directed epoxidation; Steroids; trans hydrindane; Vitamin D3

Indexed keywords

ACETYLMETHYLDIVINYLCYCLOPENTANE; ALCOHOL DERIVATIVE; COLECALCIFEROL; CYCLOPENTANE DERIVATIVE; DRUG METABOLITE; EPOXIDE; INDAN DERIVATIVE; KETONE; SECOSTEROID; STEROID; UNCLASSIFIED DRUG;

EID: 32344441719     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-923607     Document Type: Article
Times cited : (11)

References (36)
  • 2
    • 0004208435 scopus 로고
    • Fieser, L. F.; Fieser, M., Eds.; Reinhold: New York
    • Steroids, 3rd ed.; Fieser, L. F.; Fieser, M., Eds.; Reinhold: New York, 1959.
    • (1959) Steroids, 3rd Ed.
  • 3
    • 0004238211 scopus 로고    scopus 로고
    • Feldman, D.; Glorieux, F. H.; Pike, J. W., Eds.; Academic Press: New York
    • (a) Vitamin D.; Feldman, D.; Glorieux, F. H.; Pike, J. W., Eds.; Academic Press: New York, 1997.
    • (1997) Vitamin D
  • 4
    • 32344447449 scopus 로고    scopus 로고
    • Norman, A. W.; Bouillon, R.; Thomasset, M., Eds.; Vitamin D Workshop, Inc., University of California Riverside: Riverside, USA
    • (b) Vitamin D Endocrine System: Structural, Biological, Genetic and Clinical Aspects; Norman, A. W.; Bouillon, R.; Thomasset, M., Eds.; Vitamin D Workshop, Inc., University of California Riverside: Riverside, USA, 2000.
    • (2000) Vitamin D Endocrine System: Structural, Biological, Genetic and Clinical Aspects
  • 5
    • 0003703308 scopus 로고
    • Zeelen, F. J., Ed.; Elsevier: Amsterdam
    • (a) Medicinal Chemistry of Steroids; Zeelen, F. J., Ed.; Elsevier: Amsterdam, 1990.
    • (1990) Medicinal Chemistry of Steroids
  • 27
    • 32344440359 scopus 로고    scopus 로고
    • See ref. 5o
    • (c) See ref. 5o.
  • 30
    • 32344444858 scopus 로고    scopus 로고
    • note
    • First, we considered a ketone-directed epoxidation of 5. Various attempts performed with meta-chloroperbenzoic acid at r.t. led to a 50:50 mixture of two monoepoxide diastereoisomers, resulting from a total lack of facial selectivity.
  • 31
    • 32344437898 scopus 로고    scopus 로고
    • note
    • 3): δ = 13.1, 17.9, 24.7, 28.3, 46.5, 48.8, 50.7, 51.8, 52.6, 72.6, 115.8, 139.0.
  • 33
    • 32344437779 scopus 로고    scopus 로고
    • CCDC reference number: CCDC 272821
    • CCDC reference number: CCDC 272821.
  • 36
    • 32344448061 scopus 로고    scopus 로고
    • note
    • +. CCDC reference number: CCDC 272822.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.