An efficient and general route to gem-difluoromethylenated α,β-unsaturated δ-lactones: High enantioselective synthesis of gem-difluoromethylenated goniothalamins

Journal of Organic Chemistry

Volumn 71, Issue 19, 2006, Pages 7261-7267

  You, Zheng Wei ^a   Jiang, Zhong Xing ^a   Wang, Bing Lin ^a   Qing, Feng Ling ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b DONGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALDEHYDES; CATALYSIS; HYDROGENATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CINNAMALDEHYDE; DIFLUOROMETHYLENATED GONIOTHALAMINS; ENANTIOSELECTIVE SYNTHESIS; HOMOPROPARGYLIC ALCOHOLS;

KETONES;

2,2,6,6 TETRAMETHYL 1 PIPERIDINYLOXY; ACETOXYIODOBENZENE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; AROMATIC COMPOUND; BENZENE DERIVATIVE; CARBENE; CINNAMALDEHYDE DERIVATIVE; FLUORINE DERIVATIVE; IODINE DERIVATIVE; LACTONE DERIVATIVE; PIPERIDINE DERIVATIVE; QUINOLINE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; DEPROTECTION REACTION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; OXIDATION; PSEUDOMONAS; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

FURANS; HYDROCARBONS, FLUORINATED; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33749024147     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061012r     Document Type: Article

References (38)

1. For a review see: Davies-Coleman, M. T.; Rivett, D. E. A. Prog. Chem. Org. Nat. Prod. 1989, 55, 1-33.
2. (a) de Fatima, A.; Kohn, L. K.; Antonio, M. A.; de Carvalho, J. E.; Pilli, R. A. Bioorg. Med. Chem. 2005, 13, 2927-2933.
3. (b) Chen, W.-Y.; Wu, C.-C.; Lan, Y.-H.; Chang, F.-R.; Teng, C.-M.; Wu, Y.-C. Eur. J. Pharmacol. 2005, 522, 20-29.
4. (c) de Fatima, A.; Kohn, L. K.; Antonio, M. A.; de Carvalho, J. E.; Pilli, R. A. Bioorg. Med. Chem. 2006, 14, 622-631.
5. (d) Chan, K. M.; Rajab, N. F.; Ishak, M. H. A.; Ali, A. M.; Yusoff, K.; Din, L. B.; Inayat-Hussain, S. H. Chem.-Biol. Interact. 2006, 159, 129-140.
6. (a) Lewy, D. S.; Gauss, C. M.; Soenen, D. R.; Boger D. L. Curr. Med. Chem. 2002, 9, 2050-2032.
7. (b) Buck, S. B.; Hardouin, C.; Ichikawa, S.; Soenen, D. R.; Gauss, C.-M.; Hwang, I.; Swingle, M. R.; Bonness, K. M.; Honkanen, R. E.; Boger, D. L. J. Am. Chem. Soc. 2003, 125, 15694-15695.
8. (c) Maki, K.; Motoki, R.; Fujii, K.; Kanai, M.; Kobayashi, T.; Tamura, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 17111-17117.
9. Kumar, P.; Naidu, S. V. J. Org. Chem. 2006, 71, 3935-3941 and references therein.
10. For recent examples see: (a) Nicolaou, K. C.; Pihko, P. M.; Bernal, F.; Frederick, M. O.; Qian, W.; Uesaka, N.; Diedrichs, N.; Hinrichs, J.; Koftis, T. V.; Loizidou, E.; Petrovic, G.; Rodriquez, M.; Sarlah, D.; Zou, N. J. Am. Chem. Soc. 2006, 128, 2244-2257.
11. (b) Khalaf, J. K.; Datta, A. J. Org. Chem. 2005, 70, 6937-6940.
12. (c) Ramachandran, P. V.; Prabhudas, B.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2004, 69, 6294-6304.
13. (a) Ojima, I. ChemBioChem 2004, 5, 628-635.
14. (b) Böhm, H.-J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637-643.
15. (c) Strunecká, A.; Patoèka, J.; Connett, P. J. Appl. Biomed. 2004, 2, 141-150.
16. (a) Percy, J. M. Chim. Oggi. 2004, 22, 18-20.
17. (b) Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683.
18. For examples see: (a) Chupp, J. P.; Molyneaux, J. M. J. Heterocycl. Chem. 1989, 26, 1771-1780.
19. Hu, Q.-S.; Hu, C.-M. J. Fluorine Chem. 1997, 83, 87-88.
20. (c) Peng, W.; Zhu, S. Tetrahedron 2003, 59, 4395-4404.
21. You, Z.-W.; Wu, Y.-Y.; Qing, F.-L. Tetrahedron Lett. 2004, 45, 9479-9481.
22. Kirihara, M.; Takuwa, T.; Takizawa, S.; Momose, T.; Nemoto, H. Tetrahedron 2000, 56, 8275-8280.
23. (a) Gruttadauria, M.; Meo, P. L.; Noto, R. Tetrahedron Lett. 2004, 45, 83-85.
24. (b) Sundby, E.; Anthonsen, T.; Hansen, T. V. et al. Tetrahedron 2004, 60, 521-524.
25. (a) Kwok, P.-Y.; Muellner, F. W.; Chen, C.-K.; Fried, J. J. Am. Chem. Soc. 1987, 109, 3684-3692.
26. (b) Rim, I.; Cantacuzene, D.; Wakselman, C. J. Chem. Soc., Perkin Trans. 1 1982, 1063.
27. Wang, Z. G.; Hammond, G. B. J. Org. Chem. 2000, 65, 6547-6552.
28. For related examples see: (a) Itoh, T.; Kudo, K.; Tanaka, N.; Sakabe, K.; Takagi, Y.; Kihara, H. Tetrahedron Lett. 2000, 41, 4591-4595.
29. (b) Kirihara, M.; Kawasaki, M.; Katsumata, H.; Kakuda, H.; Shiro, M.; Kawabata, S. Tetrahedron: Asymmetry 2002, 13, 2283-2289.
30. (c) Itoh, T.; Kudo, K.; Yokota, K.; Tanaka, N.; Hayase, S.; Renou, M. Eur. J. Org. Chem. 2004, 406-412.
31. (d) Kaneda, T.; Komura, S.; Kitazume, T. J. Fluorine Chem. 2005, 126, 17-26.
32. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129-6139.
33. Hansen, T. M.; Florence, G. J.; Lugo-Mas, P.; Chen, J.; Abrams, J. N.; Forsyth, C. J. Tetrahedron Lett. 2003, 44, 57-59.
34. (a) Goh, S. H.; Ee, G. C. L.; Chuah, C. H.; Wei, C. Aust. J. Chem. 1995, 48, 199-205.
35. (b) Peng, X.; Li, A.; Shen, H.; Wu, T.; Pan, X. J. Chem. Res. Synop. 2002, 330-332.
36. (c) Lan, Y.-H.; Chang, F.-R.; Yu, J.-H.; Yang, Y.-L.; Chang, Y.-L.; Lee, S.-J.; Wu, Y.-C. J. Nat. Prod. 2003, 66, 487-490.
37. You, Z.-W.; Zhang, X.-G.; Qing, F.-L. Synthesis, 2006, 2533-2542.
38. Manthati, V. L.; Gree, D.; Gree, R. Eur. J. Org. Chem. 2005, 3825-3829.