Total synthesis of coronafacic acid through 6-endo-trig mode intramolecular cyclization of an enone-aldehyde to a hydrindanone using samarium(II) iodide

Tetrahedron Letters

Volumn 41, Issue 26, 2000, Pages 5115-5118

  Sono, Masakazu ^a   Hashimoto, Atsuko ^a   Nakashima, Katsuyuki ^a   Tori, Motoo ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Biologically active compounds; Carboxylic acids and derivatives; Esters; Indanes hydrindanes

Indexed keywords

ALDEHYDE DERIVATIVE; CORONAFACIC ACID; HYDROXYL GROUP; INDANONE DERIVATIVE; SAMARIUM DIIODIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CIS ISOMER; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0034709611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00786-3     Document Type: Article

References (30)

1. A part of this work was reported in The 41st symposium on the chemistry of terpenes, essential oils, and aromatics, (Iwate); Abstract Paper pp. 68-69 (1997).
2. A part of this work was reported in The 43rd symposium on the chemistry of terpenes, essential oils, and aromatics 43rd (Oita); Abstract Paper pp. 298-299 (1999).
3. Sono, M.; Nakashiba, Y.; Nakashima, K.; Tori, M. J. Org. Chem. 2000, 65, 3099-3106.
4. For 4-exo-trig cyclization: Johnston, D.; McCusker, C. M.; Procter, D. J. Tetrahedron Lett. 1999, 40, 4913-4916.
5. For 5-exo-trig cyclization: (a) Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063-1066. (b) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532-5534. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111-5113. (d) Sakai, H.; Hagiwara, H.; Ito, Y.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1999, 40, 2965-2968.
6. For 5-exo-trig cyclization: (a) Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063-1066. (b) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532-5534. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111-5113. (d) Sakai, H.; Hagiwara, H.; Ito, Y.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1999, 40, 2965-2968.
7. For 5-exo-trig cyclization: (a) Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063-1066. (b) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532-5534. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111-5113. (d) Sakai, H.; Hagiwara, H.; Ito, Y.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1999, 40, 2965-2968.
8. For 5-exo-trig cyclization: (a) Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063-1066. (b) Kan, T.; Hosokawa, S.; Nara, S.; Oikawa, M.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5532-5534. (c) Kan, T.; Nara, S.; Ito, S.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 5111-5113. (d) Sakai, H.; Hagiwara, H.; Ito, Y.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1999, 40, 2965-2968.
9. For 6-exo-trig cyclization: Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1993, 158-162.
10. For 7-exo-trig cyclization: (a) Fukuzawa, S.; Iida, M.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commun. 1987, 920-921. (b) Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc., Perkin Trans. 1 1988, 1669-1675.
11. For 7-exo-trig cyclization: (a) Fukuzawa, S.; Iida, M.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commun. 1987, 920-921. (b) Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc., Perkin Trans. 1 1988, 1669-1675.
12. Ichihara, A.; Shiraishi, K.; Nishiyama, K.; Sakai, R. J. Am. Chem. Soc. 1977, 99, 636-637.
13. Ichihara, A.; Kimura, R.; Moriyasu, K.; Sakamura, S. Tetrahedron Lett. 1977, 4331-4334.
14. Ichihara, A.; Kimura, R.; Moriyasu, K.; Sakamura, S. J. Am. Chem. Soc. 1980, 102, 6353-6355.
15. Jung, M. E.; Hudspeth, J. P. J. Am. Chem. Soc. 1980, 102, 2463-2464.
16. Jung, M. E.; Halweg, K. M. Tetrahedron Lett. 1981, 22, 2735-2738.
17. Nakayama, M.; Ohira, S.; Okamura, Soga, S. Chem. Lett. 1981, 731-732.
18. Nakayama, M.; Ohira, S. Agric. Biol. Chem. 1983, 47, 1689-1690.
19. Liu, H. J.; Brunet, M. L. Can. J. Chem. 1984, 62, 1747-1750.
20. Ohira, S. Bull. Chem. Soc. Jpn. 1984, 57, 1902-1907.
21. Bhamare, N. K.; Granger, T.; Macas, T. S.; Yates, P. J. Chem. Soc., Chem. Commun. 1990, 739-740.
22. Yates, P.; Bhamare, N. K.; Granger, T.; Macas, T. S. Can. J. Chem. 1993, 71, 995-1001.
23. Mehta, G.; Praveen, M. J. Chem. Soc., Chem. Commun. 1993, 1573-1575.
24. Nara, S.; Toshima, H.; Ichihara, A. Tetrahedron Lett. 1996, 37, 6745-6748.
25. Hoelder, S.; Blechert, S. Synlett 1996, 505-506.
26. Nara, S.; Toshima, H.; Ichihara, A. Tetrahedron 1997, 53, 9509-9524.
27. This reaction yielded four compounds (2:12:13:14=50:18:19:13), whose structures were unambiguously determined by 2D NMR after separation (HPLC). Compounds 12-14 can also be used for synthesis.
28. The minor product was the normal ketal 15, the yields of 8 and 15 being 56 and 12%, respectively.
29. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302.
30. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1985, 26, 1109-1112.