Highly regioselective and diastereoselective photooxygenation of α-cyclogeranyl derivatives

Synlett

Volumn , Issue 12, 2005, Pages 1857-1860

  Tsangarakis, Constantinos ^a   Zaravinos, Ioannis Panagiotis ^a   Stratakis, Manolis ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

Allylic hydroperoxides; Diastereoselectivity; Ene reaction; Regioselectivity; Singlet oxygen

Indexed keywords

ALLYL COMPOUND; ALLYLIC HYDROPEROXIDE; ALPHA CYCLOGERANIOL; ALPHA CYCLOGERANYL DERIVATIVE; BENZENE DERIVATIVE; GERANIOL; HYDROPEROXIDE DERIVATIVE; METHYLENE BLUE; N PHENYLTRIAZOLINEDIONE; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CIS ISOMER; OXYGENATION; PHOTOOXIDATION;

EID: 23644455459     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871573     Document Type: Article

References (21)

1. (a) Stratakis, M.; Orfanopoulos, M. Tetrahedron 2000, 56, 1595.
2. (b) Clennan, E. L. Tetrahedron 2000, 56, 9151.
3. 2 ene reactions in organic synthesis, see: (a) Nakano, M.; Furuichi, N.; Mori, H.; Katsumura, S. Tetrahedron Lett. 2001, 42, 7307.
4. (b) Griesbeck, A. G.; El-Idreesy, T. T.; Fiege, M.; Brun, R. Org. Lett. 2002, 4, 4193.
5. (c) Vassilikogiannakis, G.; Stratakis, M. Angew. Chem. Int. Ed. 2003, 42, 5465.
6. (d) Fröhlich, L.; Linker, T. Synlett 2004, 2725.
7. (e) Cordova, A.; Sunden, H.; Engqvist, M.; Ibrahem, I.; Casas, J. J. Am. Chem. Soc. 2004, 726, 8914.
8. Stratakis, M. Curr. Org. Synth. 2005, 2, 281.
9. Prein, M.; Adam, W. Angew. Chem., Int. Ed. Engl. 1996, 708, 519.
10. Linker, T.; Fröhlich, L. J. Am. Chem. Soc. 1995, 777, 2694.
11. (a) Compounds 1 and 3-5 were prepared by trivial organic methodology from α-cyclogeranyl acetate (2), which was obtained by cyclization of geranyl acetate promoted by zeolite NaY. See: Tsangarakis, C.; Stratakis, M. Adv. Synth. Catal. 2005, in press.
12. 4.
13. 1H NMR: δ = 7.89 (br s, 1 H), 5.11 (br s, 1 H), 4.83 (br s, 1 H), 4.45 (br t, 1 H, J = 5.0 Hz).
14. Adam, W.; Griesbeck, A. G.; Wang, X. Liebigs Ann. Chem. 1992, 193.
15. Stratakis, M.; Orfanopoulos, M. Tetrahedron Lett. 1995, 36, 4291.
16. Snowden, R. L.; Eichenberger, J.-C.; Linder, S. M.; Sonnay, P.; Vial, C.; Schulte-Elte, K. H. J. Org. Chem. 1992, 57, 955.
17. (a) Fehr, C. Angew. Chem. Int. Ed. 1998, 37, 2407.
18. (b) Washington, I.; Houk, K. N. Angew. Chem. Int. Ed. 2001, 40, 4485.
19. Vougioukalakis, G.G.; Orfanopoulos, M. Synlett 2005, 713.
20. 1H NMR: δ = 8.55 (br s, 1 H), 7.35-7.55 (m, 5 H), 4.64 (t, l H, J = 6.0 Hz), 1.63 (s, 3 H), 1.02 (s, 3 H), 1.00 (s, 3 H).
21. Elemes, Y.; Stratakis, M.; Orfanopoulos, M. Tetrahedron Lett. 1997, 38, 6437.