Three rings in one step: A quick approach to IKD-8344

Angewandte Chemie - International Edition

Volumn 51, Issue 20, 2012, Pages 4968-4971

  Zou, Yang ^a   Wu, Yikang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

cyclizations; eliminations; natural products; ring closing reactions; total synthesis

Indexed keywords

CYCLIZATIONS; ELIMINATIONS; NATURAL PRODUCTS; RING-CLOSING REACTIONS; TOTAL SYNTHESIS;

KETONES;

O RINGS;

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; FURAN DERIVATIVE; IKD 8344;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; CATALYSIS; CYCLIZATION; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 84860843788     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201201395     Document Type: Article

References (23)

1. Y. Minami, K. Yoshida, R. Azuma, M. Nishii, J. Inagaki, F. Nohara, Tetrahedron Lett. 1992, 33, 7373-7376
2. T. Ishida, Y. In, M. Nishii, Y. Minami, Chem. Lett. 1994, 1321-1322.
3. E. I. Hwang, B. S. Yun, W. H. Yeo, S. H. Lee, J. S. Moon, Y. K. Kim, S. J. Lim, S. U. Kim, J. Microbiol. Biotechnol. 2005, 15, 909-912 (No optical rotation data was given).
4. W. H. Kim, S. K. Hong, S. M. Lim, M.-A. Ju, S. K. Jung, Y. W. Kim, J. H. Jung, M. S. Kwon, E. Lee, Angew. Chem. 2006, 118, 7230-7233
5. Angew. Chem. Int. Ed. 2006, 45, 7072-7075
6. W. H. Kim, S. K. Hong, S. M. Lim, M.-A. Ju, S. K. Jung, Y. W. Kim, J. H. Jung, M. S. Kwon, E. Lee, Tetrahedron 2007, 63, 9784-9801. For the synthesis of fragments, see
7. W. Jiang, D. A. Lantrip, P. L. Fuchs, Org. Lett. 2000, 2, 2181-2184.
8. Y.-K. Wu, Y.-P. Sun, Org. Lett. 2006, 8, 2831-2834.
9. G.-B. Ren, Y.-K. Wu, Org. Lett. 2009, 11, 5638-5641
10. G.-B. Ren, Y.-X. Huang, Y.-P. Sun, Z.-H. Li, Y.-K. Wu, J. Org. Chem. 2010, 75, 5048-5064
11. G.-B. Ren, Y.-K. Wu, Chin. J. Chem. 2010, 28, 1651-1659.
12. For a practical access to 6, see:, Y.-K. Wu, Y.-Q. Yang, Q. Hu, J. Org. Chem. 2004, 69, 3990-3992.
13. M. T. Crimmins, K. Chaudhary, Org. Lett. 2000, 2, 775-777
14. M. T. Crimmins, B. W. King, E. A. Tabet, K. Chaudhary, J. Org. Chem. 2001, 66, 894-902.
15. M. T. Crimmins, J. She, Synlett 2004, 1371-1373.
16. G. Stork, K. Zhao, Tetrahedron Lett. 1989, 30, 287-290.
17. N. R. Guz, A. J. Phillips, Org. Lett. 2002, 4, 2253-2256
18. Y. Zhang, T. Sammakia, Org. Lett. 2004, 6, 3139-3141
19. M. T. Crimmins, M. Shamszad, Org. Lett. 2007, 9, 149-152.
20. C. Le Sann, D. M. Munoz, N. Saunders, T. J. Simpson, D. I. Smith, F. Soulas, P. Watts, C. L. Willis, Org. Biomol. Chem. 2005, 3, 1719-1728.
21. H. Fuwa, M. Sasaki, Org. Lett. 2010, 12, 584-587.
22. D. A. Evans, K. T. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988, 110, 3560-3578.
23. A full description of the specific rotation for the natural IKD-8344 can be found in:, M. Nishii, (Ikeda Mohando Co., Ltd.) Jpn. Kokai Tokkyo Koho, JP 02009382, 1990; Chem. Abstr. 1990, 113, 103380. This patent appeared to have been overlooked during the previous synthetic studies because only the incomplete rotation data (without the solvent) from Ref. [1a] was ever cited.