Ring closing metathesis directed synthesis of (R)-(-)-muscone from (+)- citronellal

Tetrahedron

Volumn 56, Issue 26, 2000, Pages 4397-4403

  Kamat, Vijayendra P ^a   Hagiwara, Hisahiro ^a   Katsumi, Tomoko ^a   Hoshi, Takashi ^a   Suzuki, Toshio ^a   Ando, Masayoshi ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

Catalysis; Cyclic ketones; Cycloalkanes; Metathesis; Ruthenium and compounds

Indexed keywords

CITRONELLAL; MUSCONE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034705481     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00333-1     Document Type: Article

References (41)

1. (a) Walbaum, H. J. J. Prakt. Chem. 1906, 73, 488.
2. (b) Ruzicka, L. Helv. Chim. Acta 1926, 9, 715, 1008.
3. Stallberg-Stenhagen S. Arkiv Kemi. 3:1951;517.
4. Djerassi C., Krankoner G.W. J. Am. Chem. Soc. 81:1959;237.
5. For some earlier racemic synthesis see: (a) Nair, M. S. R.; Mathur, H. H.; Bhattacharyya, S. C. J. Chem. Soc. 1964, 4154.
6. (b) Ohloff, G.; Becker, J.; Schulte-Elte, K. H. Helv. Chim. Acta 1967, 50, 705.
7. (c) Eschenmoser, A.; Felix, O.; Ohloff, G. Helv. Chim. Acta 1967, 50, 708.
8. (d) Yoshii, E.; Kimoto, S. Chem. Pharm. Bull. 1969, 17, 629.
9. (e) Nozaki, H.; Yamamoto, Y.; Mori, T. Can. J. Chem. 1969, 47, 1107.
10. (f) Mookherjee, B. D.; Patel, R. R.; Ledig, W. O. J. Org. Chem. 1971, 36, 4124.
11. (g) Backer, R.; Cookson, R. C.; Winston, J. R. J. Chem. Soc., Chem. Commun. 1974, 515.
12. (h) Hiyama, T.; Mishima, T.; Kitatani, K.; Nozaki, H. Tetrahedron Lett. 1974, 3297.
13. (i) Stork, G.; Macdonald, T. L. J. Am. Chem. Soc. 1975, 97, 1264.
14. (j) Takahashi, T.; Machida, K.; Kido, Y.; Nagashima, K.; Ebata, S.; Doi, T. Chem. Lett. 1997, 1291 and the references cited therein.
15. For some earlier synthesis of (R)-(-)-muscone see: (a) Mamdapur, V. R.; Pal, P. P.; Chakravarti, K. K.; Nayak, U. G.; Bhattacharyya, S. C. Tetrahedron 1964, 20, 2601.
16. (b) Branca, Q.; Fishli, A. Helv. Chim. Acta 1977, 60, 925.
17. (c) Abad, A.; Arno, M.; Pardo, A.; Pedro, J. R.; Seoane, E. Chem. Ind. 1985, 29.
18. (d) Nelson, K. A.; Mash, E. A. J. Org.Chem. 1986, 51, 2721.
19. (e) Nozawa, H.; Nohira, H. J. Org. Chem. 1987, 52, 1630.
20. (f) Xie, Z.-F.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1988, 1638.
21. (g) Xie, Z.-F.; Sakai, K. J. Org. Chem. 1990, 55, 820.
22. (h) Tanaka, K.; Ushino, H.; Kawabata, Y.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1991, 1445.
23. (i) Dowd, P.; Choi, S. C. Tetrahedron 1992, 48, 4773.
24. (j) Tanaka, K.; Matsui, J.; Somemiya, K. Synlett. 1994, 351.
25. (k) Xie, B. H.; Lu, S. J.; Fu, H. X.; Gao, L. Chin. Chem. Lett. 1997, 8, 477.
26. (l) Alexakis, A; Benhaim, C; Fournioux, X; van der Heuvel, A.; Leveque, J.-M.; March, S.; Rosset, S. Synlett 1999, 1811.
27. Porter N.A., Lacher B., Chang V.H.-T., Magnin D.R. J. Am. Chem. Soc. 111:1989;8309.
28. Ogawa T., Fang C.-L., Suemune H., Sakai K. J. Chem. Soc., Chem. Commun. 1988;1638.
29. Oppolzer W., Radinov W. J. Am. Chem. Soc. 115:1993;1593.
30. (a) Grubbs, R. H.; Miller, J. S.; Fu, G. C. Acc. Chem. Res. 1995, 28, 466.
31. (b) Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036.
32. (c) Furstner, A. Top. Catal. 1997, 4, 285.
33. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
34. (e) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, J. Am. Chem. Soc. 1990, 112, 3875.
35. (a) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10 926.
36. (b) Meng, D.; Su, D. S.; Balog, A.; Bertinato, P.; Sorensen, E. J.; Denishefsky, S. J.; Zheng, Y.; Chou, T.; Le, L.; Horwitz, S. B. J. Am. Chem. Soc. 1997, 119, 2733.
37. (c) Meng, D.; Bertinato, D.; Balog, A.; Su, D.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10 073.
38. (d) Furstner, A.; Muller, Th. J. Org. Chem. 1998, 63, 424.
39. Kirkland T., Grubbs R.H. J. Org. Chem. 62:1997;7310.
40. Preliminary communication: Kamat, V. P.; Hagiwara, H.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 1998, 2253.
41. Nakatani Y., Kawashima K. Synthesis. 1978;147.