Synthesis and reactions of two stereoisomeric [4.5.5.5]fenestranes with bridgehead substituents

Tetrahedron

Volumn 67, Issue 21, 2011, Pages 3874-3880

  Weyermann, Philipp ^a   Keese, Reinhart ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

Elimination reactions; Fenestranes; Olefin enone photocylcoaddition; Pauson Khand cyclocarbonylation; Planarizing distortions

Indexed keywords

ALKANE DERIVATIVE; BRIDGED COMPOUND; HYDROXYL GROUP; KETOL;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; CYCLOADDITION; ELIMINATION REACTION; PRIORITY JOURNAL; RING OPENING; STEREOISOMERISM; SYNTHESIS;

EID: 79955646552     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.03.086     Document Type: Article

References (15)

1. Thommen, M, Prevot L., Eberle, M. K., Bigler, P., Keese, R., Tetrahedron, in press, doi:10.1016/j.tet.2011.03.088.
2. T. Galch, and J. Mulzer J. Am. Chem. Soc. 131 2009 452 453
3. C.S. Penkett, J.A. Woolford, I.J. Day, and M.P. Coles J. Am. Chem. Soc. 132 2010 4 5
4. C. Hulot, S. Amiri, G. Blond, P.R. Schreiner, and J. Suffert J. Am. Chem. Soc. 131 2009 13387 113398
5. C. Hulot, G. Blond, and J. Suffert J. Am. Chem. Soc. 130 2008 5046 5047
6. R. Keese Chem. Rev. 106 2006 4787 4808
7. W. Luef, and R. Keese B. Halton, Planarizing Distortions in Carbon Compounds Advances in Strain in Organic Chemistry Vol. 3 1993 JAI Press, Ltd, London 229 267
8. M. Thommen, A.L. Veretenov, R. Guidetti-Grept, and R. Keese Helv. Chim. Acta 79 1997 461 475
9. The stereoisomers 2 (and 3) are specified by the C(is) or t(rans) fused bicyclo[2.3.0] and [3.3.0]alkane subunits starting in 1 with m, n.
10. P. Weyermann, H. Stoeckli-Evans, and R. Keese Acta Crystallogr. E66 2010 o340
11. P. Macchi, R. Keese, unpublished results.
12. J. Wang, R. Guidetti-Grept, R. Keese, and H. Stoeckli-Evans Helv. Chim. Acta 80 1997 1169 1175
13. H. Gerlach, T.T. Huong, and W. Müller J. Chem. Soc., Chem. Commun. 1972 1215
14. H. Gerlach, and W. Müller Helv. Chim. Acta 55 1972 2277
15. M. Gaudemar Tetrahedron Lett. 24 1983 2749