Functionalisation of terpenoids at C-4 via organopalladium dimers: cyclopropane formation during oxidation of homoallylic σ-organopalladium intermediates with lead tetraacetate

Tetrahedron

Volumn 63, Issue 51, 2007, Pages 12608-12615

  Ramos, Susana S ^a   Almeida, Paulo ^b   Santos, Lina ^a   Motherwell, William B ^c   Sheppard, Tom D ^c   Costa, Maria do Céu ^a  

^a INETI   (Portugal)

^b UNIVERSITY OF BEIRA INTERIOR   (Portugal)

^c UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,1,4A TRIMETHYL 3,4,4A,5,6,7 HEXAHYDRONAPHTHALEN 2(1H) ONE OXIME; 3,3,4 TRIMETHYLPENT 4 EN 2 ONE OXIME; ACETIC ACID DERIVATIVE; AGLYCONE; ALKENE; CHOLESTEROL DERIVATIVE; CYCLOPROPANE; DECALIN; DIMER; DIMETHYLCHOLEST 5 EN 3 ONE OXIME; FRIEDELAN 3 ONE OXIME; FRIEDELIN; LANOSTA 8,24 DIEN 3 ONE OXIME; LANOSTEROL DERIVATIVE; LEAD TETRAACETATE; OXIME DERIVATIVE; PALLADIUM COMPLEX; SAPONIN DERIVATIVE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 35848961676     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.016     Document Type: Article

References (19)

1. Press J.B., Reynolds R.C., May R.D., and Marciani D.J. In: Atta-ur-Rahman (Ed). Structure/Function Relationships of Immunostimulating Saponins. Studies in Natural Product Chemistry Vol. 24 (2000), Elsevier Science, New York, NY 131-174
2. Soltysik S., Wu J.-Y., Recchia J., Wheeler D.A., Newman M.J., Coughlin R.T., and Kensil C.R. Vaccine 13 (1995) 1403-1410
3. Barr I.G., Sjölander A., and Cox J.C. Adv. Drug Delivery Rev. 32 (1998) 247-271
4. Pillion D.J., Amsden J.A., Kensil C.R., and Recchia J. J. Pharm. Sci. 85 (1996) 518-524
5. Marciani D.J., Press J.B., Reynolds R.C., Pathak A.K., Pathak V., Gundy L.E., Farmer J.T., Koratich M.S., and May R.D. Vaccine 18 (2000) 3141-3151
6. Constable A.G., McDonald S.W., Sawkins L.C., and Shaw B.L. J. Chem. Soc., Dalton Trans. (1980) 1992-2000
7. Baldwin J.E., Jones R.H., Najera C., and Yus M. Tetrahedron 41 (1985) 699-711
8. White A., Horsington E.J., Nedjar N., Peakman T.M., and Curiale J.A. Tetrahedron Lett. 39 (1998) 3031-3034
9. Bore L., Honda T., and Gribble G.W. J. Org. Chem. 65 (2000) 6278-6282
10. Carr K., and Sutherland J. J. Chem. Soc., Chem. Commun. (1984) 1227-1228
11. Carr K., Saxton H.M., and Sutherland J.K. J. Chem. Soc., Perkin Trans. 1 (1988) 1599-1601
12. For the oxidation procedure, see:. Paranjape B.V., and Pyle J.L. J. Org. Chem. 36 (1971) 1009-1011
13. For the oxidation of cholesterol, see:. Fieser A.L.F. Organic Syntheses, Collective Volume IV (1963), John Wiley & Sons, New York, NY
14. For dimethylation of cholestenone, see:. Duan H.-Y., Wang J.-X., and Li T.-S. Synth. Commun. 29 (1999) 3197-3205
15. Heathcock C.H., and Ellis J.E. Tetrahedron Lett. 12 (1971) 4995-4996
16. Kepler J.A., Philip A., Lee Y.W., Musallam H.A., and Carroll F.I. J. Med. Chem. 30 (1987) 1505-1509
17. Kiefer E.F., and Carlson D.A. Tetrahdron Lett. 8 (1967) 1617-1622
18. Kochi J.K. J. Org. Chem. 30 (1965) 3265-3271
19. Marciani D.J., Pathak A.K., Reynolds R.C., Seitz L., and May R.D. Int. Immunopharmacol. 1 (2001) 813-818