Asymmetric synthesis of (+)-trans-aerangis lactone

Bulletin of the Korean Chemical Society

Volumn 34, Issue 1, 2013, Pages 75-78

  Kim, Aejin ^a   Sharma, Satyasheel ^a   Kwak, Jong Hwan ^a   Kim, In Su ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Aerangis lactone; Asymmetric; Catalytic; Crotylation; Metathesis

Indexed keywords

AERANGIS LACTONE; ASYMMETRIC; CATALYTIC; CROTYLATION; METATHESIS;

ALDEHYDES; CATALYSIS; IRIDIUM; OLEFINS; RUTHENIUM;

ESTERS;

EID: 84872960971     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2013.34.1.75     Document Type: Article

References (25)

1. (a) Kaise, R. Chem. Biodiversity 2004, 1, 13.
2. (b) Galindo, J. C. G.; de Luque, A. P.; Jorrin, J.; Macias, F. A. J. Agric. Food Chem. 2002, 50, 1911.
3. Scotti, M. T.; Fernandes, M. B.; Ferreira, M. J. P.; Emerenciano, V. P. Bioorg. Med. Chem. 2007, 15, 2927.
4. Francke, W.; Schulz, S. In Comprehensive Natural Product Chemistry; Barton, D. H. R., Nakanishi, K., Eds.; Elsevier: Amsterdam, 1999; Vol. 8, p 197.
5. Miyazawa, M.; Shimabayashi, H.; Hayashi, S.; Hashimoto, S.; Nakamura, S.; Kosaka, H.; Kameoka, H. J. Agric. Food Chem. 2000, 48, 5406.
6. Entman, M. L.; Cook, J. W.; Bressler, R. Circ. Res. 1969, 24, 793.
7. (a) Chiu, P.; Leung, L. T.; Ko, B. C. B. Nat. Prod. Rep. 2010, 27, 1066.
8. (b) Florence, G. J.; Gardner, N. M.; Paterson, I. Nat. Prod. Rep. 2008, 25, 342.
9. (c) Boucard, V.; Broustal, G.; Campagne, J. M. Eur. J. Org. Chem. 2007, 225.
10. Kaiser, R. In The Scent of Orchids: Olfactory and Chemical Investigations; Elsevier: Amsterdam, 1993.
11. Kaiser, R. U.S. Patent 5,248,792, 1993.
12. Brenna, E.; Negri, C. D.; Fuganti, C.; Serra, S. Tetrahedron: Asymmetry 2001, 12, 1871.
13. Wu, Y.; Shen, X.; Tang, C.-J.; Chen, Z.-L.; Hu, Q.; Shi, W. J. Org. Chem. 2002, 67, 3802.
14. Yadav, J. S.; Rao, R. N.; Kumar, B. P.; Somaiah, R.; Ravindar, K.; Reddy, B. V. S.; Ghamdi, A. A. K. A. Synthesis 2011, 3168.
15. Beeson, T. D.; Mastracchio, A.; Hong, J.-B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582.
16. Winter, P.; Swatschek, J.; Willot, M.; Radtke, L.; Olbrisch, T.; Schäfer, A.; Christmann, M. Chem. Commun. 2011, 47, 12200.
17. (a) Sharma, S.; Park, E.; Park, J.; Kim, I. S. Org. Lett. 2012, 14, 906.
18. (b) Park, J.; Park, E.; Kim, A.; Lee, Y.; Chi, K.-W.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Org. Lett. 2011, 13, 4390.
19. (c) Park, J.; Park, E.; Kim, A.; Park, S.-A.; Lee, Y.; Chi, K.-W.; Jung, Y. H.; Kim, I. S. J. Org. Chem. 2011, 76, 2214.
20. (d) Kim, A.; Kim, I. S. Bull. Korean Chem. Soc. 2011, 32, 3748.
21. Kim, I. S.; Han, S. B.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2514.
22. For representative reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
23. (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
24. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
25. But, T. Y. S.; Toy, P. H. J. Am. Chem. Soc. 2006, 128, 9636.