Ireland-Claisen rearrangement of steroidal Δ23-22-alcohols: An application to Δ22,25-24-alkyl steroid synthesis

Tetrahedron Letters

Volumn 41, Issue 30, 2000, Pages 5765-5767

  Khripach, Vladimir A ^a   Zhabinskii, Vladimir N ^a   Konstantinova, Olga V ^a   Khripach, Natalya B ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

1,4 dienes; Ireland Claisen rearrangement; Peterson olefination; Silicon and compounds; Steroids and sterols

Indexed keywords

SILICON DERIVATIVE; STEROID; STEROL;

ANALYTIC METHOD; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; SIALYLATION; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0034702550     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00900-X     Document Type: Article

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28. 2 with hexane-EtOAc (70:1→8:1) to give the starting ester 7 (220 mg) and the acid 11 (345 mg, 50% isolated yield) as a mixture (1:3) of less polar and more polar isomers.
29. 3): δ 13.1, 13.8, 19.7, 20.0, 21.5, 22.2, 23.4, 24.9, 25.7, 29.4, 30.4, 31.2, 34.1, 35.8, 36.0, 40.8, 40.9, 43.4, 44.1, 44.4, 48.8, 56.9, 57.2, 83.1, 109.3, 132.0, 137.0, 150.5.