3aβ-Hydroxy-7aβ-methylperhydroinden-4-one Derivatives en route to Analogues of Cardenolides

Synlett

Volumn 1997, Issue 7, 1997, Pages 833-835

  Frigerio, M ^a,b   Santagostino, M ^a   Sputore, S ^a  

^a Prassis Sigma Tau Research Institute   (Italy)

^b Archimica   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002063961     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5766     Document Type: Article

References (29)

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3. 3 metabolites see: Kabat M.M., Kiegiel J., Cohen N., Toth K., Wovkulich P.M., Uskokovic M.R. J. Org. Chem. 1996, 61, 118.
4. Inhoffen H.H, Quinkert G., Siegmund S., Kampe D., Domagk G.F. Chem. Ber. 1957, 90, 664.
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7. Very few syntheses of racemic 3aβ-hydroxy-7aβ-methylperhydroinden-4-one have been reported in the literature: Johnson P.J., Priest M.A. J. Am. Chem. Soc. 1974, 96, 5618; Mellor M., Santos A., Scovell E.G., Sutherland J.K. J. Chem. Soc., Chem. Comm. 1978, 258; Amupitan J., Scovell E.G., Sutherland J.K. J. Chem. Soc., Perkin Trans .1 1983, 755.
8. Very few syntheses of racemic 3aβ-hydroxy-7aβ-methylperhydroinden-4-one have been reported in the literature: Johnson P.J., Priest M.A. J. Am. Chem. Soc. 1974, 96, 5618; Mellor M., Santos A., Scovell E.G., Sutherland J.K. J. Chem. Soc., Chem. Comm. 1978, 258; Amupitan J., Scovell E.G., Sutherland J.K. J. Chem. Soc., Perkin Trans .1 1983, 755.
9. Very few syntheses of racemic 3aβ-hydroxy-7aβ-methylperhydroinden-4-one have been reported in the literature: Johnson P.J., Priest M.A. J. Am. Chem. Soc. 1974, 96, 5618; Mellor M., Santos A., Scovell E.G., Sutherland J.K. J. Chem. Soc., Chem. Comm. 1978, 258; Amupitan J., Scovell E.G., Sutherland J.K. J. Chem. Soc., Perkin Trans .1 1983, 755.
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11. (S)-(+)-2,3,7,7a-Tetrahydro-7a-methyl-1H-indene-1,5(6H)-dione 3 is commercially available (Acros) or can be prepared from 2-methyl-1,3-cyclopentandione. Hajos Z.G., Parrish D.R. Org. Syn. Coll. 1984, 63, 26.
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14. Crude nitrile 5 was obtained as a diastereomeric mixture (α:β = 1:4, 63% yield), which could be easily separated by column chromatography and the undesired a isomer recycled to a 1:4 α/β mixture by treatment with tBuOK in 98% yield.
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29. 3): δ 14.7 (q); 20.0 (t); 22.7 (t); 25.1 (t); 37.0 (t); 40.1 (t); 49.8 (s); 50.7 (d); 64.8 (t); 65.4 (t); 65.4 (t); 83.4 (s); 118.5(d); 104.2 (d); 145.1 (s).