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Volumn 51, Issue 28, 2010, Pages 3610-3612

First total synthesis of 11-tellura steroids

Author keywords

1,8 Bis(trimethylsilyl) 2,6 octadiene; Intramolecular Diels Alder reaction; Tellura steroids; Thermolysis

Indexed keywords

STEROID; TELLURIUM DERIVATIVE;

EID: 77954348682     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.008     Document Type: Article
Times cited : (12)

References (44)
  • 31
    • 77954349249 scopus 로고    scopus 로고
    • note
    • Sodium telluride was prepared as follows: a mixture of powdered tellurium (130 mg, 1.02 mmol), rongalite (sodium hydroxymethane sulfinate) (340 mg) and aqueous sodium hydroxide (70 mg in 1 mL of water) was stirred at 60 °C for 2 h under argon, to produce sodium telluride. The wine-colored solution was evaporated to dryness under reduced pressure.
  • 33
    • 77954349384 scopus 로고    scopus 로고
    • note
    • The compound 5 is sensitive to oxygen, and was stored under argon atmosphere. The latter was unstable under the conditions of silica gel chromatography and was used in the following step without further purification.
  • 34
    • 77954349634 scopus 로고    scopus 로고
    • note
    • The typical procedure of thermolysis is as follows: a solution of 5 (0.5 g, 1.20 mmol) in 20 mL of o-xylene was stirred under argon at 130 °C for 12 h. After cooling, the solvent was removed under pressure (1 mmHg). The resulting oil was purified by flash chromatography on silica gel (petroleum ether/diethyl ether 8:2) to afford compound 6a (0.23 g, 46%) and compound 6b (0.06 g, 12%). Those compounds are sensitive to oxygen, and were stored under an argon atmosphere.
  • 36
    • 77954349668 scopus 로고    scopus 로고
    • note
    • +]; found: 414.0852.
  • 42
    • 77954349066 scopus 로고    scopus 로고
    • note
    • For these three families of heterosteroids (11-thia, -selena and -tellura steroids), we observed an influence of the heteroatom on the Wacker oxidation reagents. In the case of 11-thia steroids, to overcome this problem, the sulfur atom was firstly oxidized before doing the Wacker oxidation. This study on 11-selena and 11-tellura steroids is under progress and will be reported in due course as a full Letter.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.