Preparation of (5R)-4,8-dimethylbicyclo[3.3.0]oct-1(8),3-dien-2-one from (-)-limonene oxide. A novel intermediate to the synthesis of 4-5-5 fused tricarbocyclic core present in terpenic natural products

Journal of the Brazilian Chemical Society

Volumn 15, Issue 5, 2004, Pages 652-657

  Pisoni, Diego S ^a   Silva, Daniel B ^a   Schenato, Rossana A ^b   Ceschi, Marco A ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b PONTIFICAL CATHOLIC UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

Bicyclo 3.3.0 octane; Building block; Chiral; Limonene oxide

Indexed keywords

4,8 DIMETHYLBICYCLO[3.3.0]OCT 1(8),3 DIEN 2 ONE; CYANOHYDRIN; KETONE; LIMONENE; LIMONENE OXIDE; TERPENE DERIVATIVE; TRICARBOXYLIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; HYDROGENATION; SYNTHESIS;

EID: 9644262399     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50532004000500007     Document Type: Article

References (24)

1. Subburaj, K.; Okamoto, S.; Sato, F.; J. Org. Chem. 2002, 67, 1024 and references therein.
2. Mehta, G.; Sreenivas, K.; Chem. Commun. 2001, 1892.
3. Mehta, G.; Srinivas, K.; Tetrahedron Lett. 1999, 40, 4877.
4. Armone, A.; Nasini, G.; Vajna de Pava, O.; J. Chem. Soc., Perkin Trans. 1 1993, 2723.
5. Schulz, S.; Messer, C.; Dettner, K.; Tetrahedron Lett. 1997, 38, 2077.
6. König, G.M.; Wright, A.D.; J. Org. Chem. 1997, 62, 3837.
7. Nabeta, K.; Yamamoto, K.; Hashimoto, M.; Koshino, H.; Funatsuki, K.; Katoh, K.; J. Chem. Soc., Chem. Commun. 1998, 1485.
8. Warmers, U.; Wihstutz, K.; Bulow, N.; Fricke, C.; König, W.A.; Phytochemistry 1998, 49, 1723.
9. Warmers, U.; König, W.A.; Phytochemistry 1999, 52, 1519.
10. Nabeta, K.; Yamamoto, M.; Koshino, H.; Fukui, H.; Fukushi, Y.;Tahara, S.; Biosci. Biotechnol. Biochem. 1999, 63, 1112.
11. Fietz-Razavian, S.; Schulz, S.; Dix. I.; Jones, P. G.; Chem. Commun. 2001, 2154.
12. Mehta, G.; Srinivas, K.; Tetrahedron Lett. 2001, 42, 2855.
13. Piers, E.; Orellana, A.; Synthesis 2001, 2138.
14. Takayanagi, H.; Kitano, Y.; Morinaka, Y.; J. Org. Chem. 1994, 59, 2700.
15. Stork, G.; Depezay, J.C.; d'Angelo, J.; Tetrahedron Lett. 1975, 6, 389.
16. Takahashi, T.; Nemoto, H.; Kanda, Y.; Tsuji, J.; Tetrahedron 1987, 43, 5499.
17. Sakai, K.; Ishiguro, Y.; Funakoshi, K.; Ueno, K.; Suemune, H.; Tetrahedron Lett. 1984, 25, 961.
18. Hedge, S. G.; Wolinsky J.; J. Org. Chem. 1982, 47, 3148.
19. Wolinsky J.; Barker, W.; J. Am. Chem. Soc. 1960, 82, 636.
20. Wolinsky J.; Slabaugh, M. R.; Gibson, T.; J. Org. Chem. 1964, 29, 3740.
21. Paquette, L.A.; Liang, S.; Wang, H.L.; J. Org. Chem. 1996, 61, 3268.
22. Davis, C.E.; Duffy, B.C.; Coates, R.M.; Org. Lett. 2000, 2, 2717.
23. Agosta, W.C.; Wolff, S.; J. Org. Chem. 1975, 40, 1699.
24. Suemune, H.; Oda, K.; Saehi, S.; Sakai, K.; Chem. Pharm. Bull. 1988, 36, 172.