Androstanes with modified carbon skeletons

European Journal of Organic Chemistry

Volumn , Issue 24, 2011, Pages 4543-4550

  Norden, Sascha ^a   Bender, Matthias ^a   Rullkötter, Jürgen ^a   Christoffers, Jens ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

A nor steranes; Androstanes; Estranes; Fossil biomarkers; Hydrocarbons; Ring contraction

Indexed keywords

EID: 80051541940     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100390     Document Type: Article

References (33)

1. E. Grosjean, G. D. Love, C. Stalvies, D. A. Fike, R. E. Summons, Org. Geochem. 2009, 40, 87-100.
2. For overviews, see: a) S. M. Gaines, G. Eglinton, J. Rullkötter, Echoes of Live: What Fossil Molecules Reveal About Earth History, Oxford University Press, New York, 2008;
3. b) K. E. Peters, C. C. Walters, J. M. Moldowan, The Biomarker Guide, Cambridge University Press, Cambridge, 2005;
4. c) S. C. Brassell, G. Eglinton, J. R. Maxwell, Biochem. Soc. Trans. 1983, 11, 575-586.
5. a) W. Xie, H. Peng, D.-I. Kim, M. Kunkel, G. Powis, L. H. Zalkow, Bioorg. Med. Chem. 2001, 9, 1073-1083;
6. b) D. Klomp, K. Djanashvili, N. C. Svennum, N. Chantapariyavat, C.-S. Wong, F. Vilela, T. Maschmeyer, J. A. Peters, U. Hanefeld, Org. Biomol. Chem. 2005, 3, 483-489.
7. For a review, see: B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863-927.
8. A. Kuhl, W. Kreiser, Helv. Chim. Acta 1998, 81, 2264-2269.
9. H. J. Nicholas, J. Org. Chem. 1958, 23, 1747-1749.
10. a) N. G. Aher, R. G. Gonnade, V. S. Pore, Synlett 2009, 2005-2009;
11. b) R. Jogireddy, J. Rullkötter, J. Christoffers, Synlett 2007, 2847-2850.
12. a) A. L. Wilds, N. A. Nelson, J. Am. Chem. Soc. 1953, 75, 5360-5365;
13. b) C. Djerassi, P. A. Hart, C. Beard, J. Am. Chem. Soc. 1965, 87, 85-90;
14. c) for a review, see: H. Pellissier, M. Santelli, Org. Prep. Proced. Int. 2002, 34, 609-642.
15. a) Huang-Minlon, J. Am. Chem. Soc. 1946, 68, 2487-2488;
16. b) Huang-Minlon, J. Am. Chem. Soc. 1949, 71, 3301-3303.
17. M. Pelecanou, S. Nicolaropoulos, Z. Naturforsch., Teil B 1993, 48, 1305-1306.
18. a) K. Ueno, Chem. Pharm. Bull. 1964, 12, 92-100;
19. b) S. A. Julia, H. Heusser, Helv. Chim. Acta 1952, 35, 2080-2089;
20. c) L. Ruzicka, P. Meister, V. Prelog, Helv. Chim. Acta 1947, 30, 867-878.
21. E. J. Corey, J. W. Suggs, Tetrahedron Lett. 1975, 16, 2647-2650.
22. A. K. Bose, P. Mangiaracina, Tetrahedron Lett. 1987, 28, 2503-2506.
23. G. van Graas, F. de Lange, J. W. de Leeuw, P. A. Schenck, Nature 1982, 296, 59-61.
24. L. Ruzicka, V. Prelog, P. Meister, Helv. Chim. Acta 1945, 28, 1651-1660.
25. N. Pappas, H. R. Nace, J. Am. Chem. Soc. 1959, 81, 4556-4561.
26. a) H. M. C. Ferraz, L. F. Silva Jr., J. Org. Chem. 1998, 63, 1716-1718;
27. b) H. M. C. Ferraz, L. F. Silva Jr., J. Braz. Chem. Soc. 2001, 12, 548-551;
28. c) for a review, see: L. F. Silva Jr., V. M. T. Carneiro, Synthesis 2010, 1059-1074.
29. M.-L. Bennasar, B. Vidal, R. Kumar, A. Lazaro, J. Bosch, Eur. J. Org. Chem. 2000, 3919-3925.
30. J. Fishman, J. Org. Chem. 1962, 27, 1745-1749.
31. H.-J. Schneider, U. Buchheit, N. Becker, G. Schmidt, U. Siehl, J. Am. Chem. Soc. 1985, 107, 7027-7039.
32. S. Sarkar, S. Gosh, Tetrahedron 1994, 50, 921-930.
33. M. Ratier, B. Jousseaume, N. Noiret, N. Petit, J.-C. Lartigue, M. Petraud, Magn. Reson. Chem. 1993, 31, 176-181.