A convenient access to thermodynamically nonstabilised spiroketal isomers: The first synthesis of (Z)-7-methyl-1,6-dioxaspiro[4.5]decane

Tetrahedron Letters

Volumn 46, Issue 46, 2005, Pages 7923-7926

  Doubský, Jan ^a   Šaman, David ^a   Zedník, Jiří ^b   Vašíčková, Soňa ^a   Koutek, Bohumír ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Alkynones; Diastereoselective synthesis; Nonstabilised isomers; Spiroketals

Indexed keywords

7 METHYL 1,6 DIOXASPIRO[4.5]DECANE; ALKANE DERIVATIVE; DECANE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; HYDROGENATION; ISOMER; SYNTHESIS; THERMODYNAMICS;

EID: 26844495248     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.085     Document Type: Article

References (19)

1. For reviews of spiroketals, see: F. Perron, and K.F. Albizati Chem. Rev. 89 1989 1617 1661
2. M.F. Jacobs, and W. Kitching Curr. Org. Chem. 2 1998 395 436
3. W. Francke, and W. Kitching Curr. Org. Chem. 5 2001 233 251
4. K.T. Mead, and B.N. Brewer Curr. Org. Chem. 7 2003 227 256
5. S.K. Ghosh, R.P. Hsung, and J. Liu J. Am. Chem. Soc. 127 2005 8260 8261
6. J. Chen, M.T. Fletcher, and W. Kitching Tetrahedron: Asymmetry 6 1995 967 972
7. Q.-H. Zhang, T. Tolasch, F. Schlyter, and W. Francke J. Chem. Ecol. 28 2002 1839 1852
8. P.M. Pihko, and J.E. Aho Org. Lett. 6 2004 3849 3852
9. J. Doubský, L. Streinz, D. Šaman, J. ZednIÍk, and B. Koutek Org. Lett. 6 2004 4909 4911
10. J. Doubský, L. Streinz, L. Lešetický, and B. Koutek Synlett 2003 937 942
11. R. Jacobson, R.J. Taylor, H.J. Williams, and L.R. Smith J. Org. Chem. 47 1982 3140 3142
12. 2O).
13. -1.
14. W. Kitching, J.A. Lewis, M.V. Perkins, R. Drew, Ch.J. Moore, V. Schurig, W.A. König, and W. Francke J. Org. Chem. 54 1989 3893 3902
15. W. Francke, W. Reith, and V. Sinnwell Chem. Ber. 113 1980 2686 2693
16. P. Deslongchamps, D.D. Rowan, N. Pothier, T. Sauvé, and J.K. Saunders Can. J. Chem. 59 1981 1105 1121
17. N. Pothier, S. Goldstein, and P. Deslongchamps Helv. Chim. Acta 75 1992 604 620
18. + or Lewis acid) essential for the acetal formation still remains unclear. Some plausible explanations are: trace amounts of acetic acid present as impurity in the solvents, acidic nature of the glassware used or small traces of HCl present in the palladium catalyst (cf. Ref. 13).
19. M.A. Brimble, J.H. Park, and C.M. Taylor Tetrahedron 59 2003 5861 5868