A formal total synthesis of (±)-halichlorine and (±)-pinnaic acid

Organic Letters

Volumn 6, Issue 6, 2004, Pages 965-968

  Matsumura, Yosuke ^a   Aoyagi, Sakae ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 AZASPIRO[4.5]DECANE DERIVATIVE; ALKENE; AZASPIROBICYCLIC KETONE; DECANE; HALICHLORINE; KETONE DERIVATIVE; LACTAM DERIVATIVE; METHYLTRIFLATE; PINNAIC ACID; QUINOLIZIDINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HYDROGENATION; METHYLATION; PRECURSOR; RING OPENING; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 1642487641     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0301431     Document Type: Article

References (33)

1. (a) Kuramoto, M.; Tong, C.; Yamada, K.; Chiba, T.; Hayashi, Y.; Uemura, D. Tetrahedron Lett. 1996, 37, 3867-3870.
2. (b) Arimoto, H.; Hayakawa, I.; Kuramoto, M.; Uemura, D. Tetrahedron Lett. 1998, 39, 861-862.
3. Chou, T.; Kuramoto, M.; Otani, Y.; Shikano, M.; Yazawa, K.; Uemura, D. Tetrahedron Lett. 1996, 37, 3871-3874.
4. (a) Lee, S.; (Spring) Zhao, Z. Org. Lett. 1999, 1, 681-683.
5. (b) Arimoto, H.; Asano, S.; Uemura, D. Tetrahedron Lett. 1999, 40, 3583-3586.
6. (c) Lee, S.; (Spring) Zhao, Z. Tetrahedron Lett. 1999, 40, 7921-7924.
7. (d) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503-8507.
8. (e) Koviach, J. L.; Forsyth, C. J. Tetrahedron Lett. 1999, 40, 8529-8532.
9. (f) Shindo, M.; Fukuda, Y.; Shishido, K. Tetrahedron Lett. 2000, 41, 929-932.
10. (g) Wright, D. L.; Schulte, J. P., II.; Page, M. A. Org. Lett. 2000, 2, 1847-1850.
11. (h) White, J. D.; Blakemore, P. R.; Korf, E. A.; Yokochi, A. F. T. Org. Lett. 2001, 3, 413-415.
12. (i) Fenster, M. D. B.; Patrick, B. O.; Dake, G. R. Org. Lett. 2001, 3, 2109-2112.
13. (j) Yokota, W.; Shindo, M.; Shishido, K. Heterocycles 2001, 54, 871-885.
14. (k) Takasu, K.; Ohsato, H.; Ihara, M. Org. Lett. 2003, 5, 3017-3020.
15. For the synthesis of halichlorine, see: (a) Trauner, D.; Danishefsky, S. J. Tetrahedron Lett. 1999, 40, 6513-6516. (b) Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1999, 38, 3542-3545. (c) Trauner, D.; Churchill, D. G.; Danishefsky, S. J. Helv. Chim. Acta 2000, 83, 2344-2351.
16. For the synthesis of halichlorine, see: (a) Trauner, D.; Danishefsky, S. J. Tetrahedron Lett. 1999, 40, 6513-6516. (b) Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1999, 38, 3542-3545. (c) Trauner, D.; Churchill, D. G.; Danishefsky, S. J. Helv. Chim. Acta 2000, 83, 2344-2351.
17. For the synthesis of halichlorine, see: (a) Trauner, D.; Danishefsky, S. J. Tetrahedron Lett. 1999, 40, 6513-6516. (b) Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1999, 38, 3542-3545. (c) Trauner, D.; Churchill, D. G.; Danishefsky, S. J. Helv. Chim. Acta 2000, 83, 2344-2351.
18. For the synthesis of pinnaic acid, see: (a) Carson, M. W.; Kim, G.; Hentemann, M. F.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4450-4452. (b) Carson, M. W.; Kim, G.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4453-4456.
19. For the synthesis of pinnaic acid, see: (a) Carson, M. W.; Kim, G.; Hentemann, M. F.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4450-4452. (b) Carson, M. W.; Kim, G.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4453-4456.
20. Hayakawa, I.; Arimoto, H.; Uemura, D. Heterocycles 2003, 59, 441-444.
21. Matsumura, Y.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3249-3252.
22. Very recently, stereoselective C7-methylation of a TES-protected tricyclic lactam with iodomethane and LDA has been reported (see ref 3k).
23. (a) Myers, A. G.; Yang, B. H.; Kopecky, D. J. Tetrahedron Lett. 1996, 37, 3623-3626.
24. 3 for lactam ring opening, see: Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem. 1998, 63, 8397-8406. Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592.
25. 3 for lactam ring opening, see: Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem. 1998, 63, 8397-8406. Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583-4592.
26. 3 has been reported (see ref 3k).
27. The difficulty of the lactam hydrolysis was also observed when the acidic conditions using concentrated HCl at 110°C in a sealed tube were applied to the methyl-protected tricyclic lactam i. Employing these reaction conditions did not effect the desired ring-opening even after a reaction time of 17 h but rather led to cleavage of the methoxy group. (Equation Presented)
28. For a review on application of perfluoroalkanesulfonic esters in organic chemistry, see: Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85-126.
29. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
30. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
31. (c) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
32. Scholl, M.; Ding, S.; Lee, C. W.; Grubss, R. H. Org. Lett. 1999, 1, 953-966.
33. For a review, see: McClinton, M. A. Aldrichim. Acta 1995, 28, 31-35.