Synthesis of a new class of spirophenanthrones

Synlett

Volumn , Issue 9, 2009, Pages 1501-1505

  Wu, Xue Song ^a   Lin, Shuang Zheng ^a   Li, Ming Zong ^a   You, Tian Pa ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

10 methylene 9 phenanthrone; Dimerization; Hetero Diels Alder reaction; Mannich bases; Polymethoxyaromatics

Indexed keywords

10 METHYLENE 9 PHENANTHRONE; 9 PHENANTHROL; AROMATIC COMPOUND; BENZALDEHYDE DERIVATIVE; CARBENE; FORMALDEHYDE; MANNICH BASE; PROLINE; SPIRO COMPOUND; SPIROPHENANTHRONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DIELS ALDER REACTION; DIMERIZATION; MICHAEL ADDITION; ONE POT SYNTHESIS;

EID: 67649416227     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217174     Document Type: Article

References (17)

1. (a) Choi, Y.-W.; Takamatsu, S.; Khan, S. I.; Srinivas, P. V.; Ferreira, D.; Zhao, J. J. Nat. Prod. 2006, 69, 356.
2. (b) Chen, M.; Kilgore, N.; Lee, K.-H.; Chen, D.-F. J. Nat. Prod. 2006, 69, 1697.
3. (a) Xia, Y.; Yang, Z.-Y.; Xia, P.; Bastow, K. F.; Kuo, S.-C.; Li, K.-H. J. Med. Chem. 1998, 41, 1155.
4. (b) Freyer, A. J.; Abu Zarga, M. H.; Firdous, S.; Shamma, M. J. Nat. Prod. 1987, 50, 684.
5. (a) Gupta, S.; Das, L.; Datta, A. B.; Poddar, A.; Janik, M. E.; Bhattacharrya, B. Biochemistry 2006, 45, 6467.
6. (b) Charlton, J. L. J. Nat. Prod. 1998, 61, 1447.
7. (a) Damu, A. G.; Kuo, P.-C.; Shi, L.-S.; Li, C.-Y.; Kuoh, C.-S.; Wu, P.-L.; Wu, T.-S. J. Nat. Prod. 2005, 68, 1071.
8. (b) Wei, L.; Shi, Q.; Bastow, K. F.; Brossi, A.; Morris-Natschke, S. L.; Nakagawa-Goto, K.; Wu, T.-S.; Pan, S.-L.; Teng, C.-M.; Lee, K.-H. J. Med. Chem. 2007, 50, 3674.
9. (c) Stark, D.; Lykkeberg, A. K.; Christensen, J.; Budnik, B. A.; Abe, F.; Jaroszewski, J. W. J. Nat. Prod. 2002, 65, 1299.
10. Bilgic, S.; Bilgic, O.; Bueyuekkidan, B.; Guenduez, M. J. Chem. Res. 2007, 2, 76.
11. Chauhan, M. S.; Mckinon, D. M. Can. J. Chem. 1981, 59, 2223.
12. (a) Weinert, E.; Dondi, R.; Colloredo-Melz, S.; Frankenfield, K. N.; Mitchell, C. H.; Freccero, M.; Rokita, S. E. J. Am. Chem. Soc. 2006, 128, 11940.
13. (b) Gardner, P. D.; Sarrafizadeh, H. R.; Brandon, R. L. J. Am. Chem. Soc. 1959, 81, 5515.
14. (a) Lin, S.-Z.; Chen, Q.-A.; You, T.-P. Synlett 2007, 2101.
15. (b) Lin, S.-Z.; You, T.-P. Tetrahedron 2008, 64, 9906.
16. 2, eluting with PE-EtOAc, to produce the dimer of 10-methylene-9-phenanthrones.
17. 2: C, 87.36; H, 4.89; O, 7.76. Found: C, 86.92; H, 4.88;