Total synthesis of IKD-8344

Angewandte Chemie - International Edition

Volumn 45, Issue 42, 2006, Pages 7072-7075

  Kim, Woo Han ^a   Hong, Sung Kil ^a   Lim, Sang Min ^a   Ju, Min Ae ^a   Jung, Soon Kyu ^a   Kim, Yong Wook ^a   Jung, Jae Hoon ^a   Kwon, Min Sang ^a   Lee, Eun ^a  

^a Seoul National University   (South Korea)

Author keywords

Anticancer agents; Antifungal agents; Macrodiolides; Natural products; Total synthesis

Indexed keywords

ETHERS; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL);

ANTICANCER AGENTS; ANTIFUNGAL AGENTS; MACRODIOLIDES; NATURAL PRODUCTS;

ANTIBIOTICS;

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC ANTIBIOTIC; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FURAN DERIVATIVE; IKD 8344; SOLVENT;

ARTICLE; CHEMISTRY; CYCLIZATION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; INFRARED SPECTROPHOTOMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STREPTOMYCES; SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTIFUNGAL; ANTIBIOTICS, ANTINEOPLASTIC; CYCLIZATION; FURANS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; SOLVENTS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, INFRARED; STREPTOMYCES;

EID: 33750625224     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602860     Document Type: Article

References (18)

1. a) Y. Minami, K. Yoshida, R. Azuma, M. Nishii, J. Inagaki, F. Nohara, Tetrahedron Lett. 1992, 33, 7373-7376;
2. b) 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.
4. For a report on the synthesis of the fragments, see: W. Jiang, D. A. Lantrip, P. L. Fuchs, Org. Lett. 2000, 2, 2181-2184.
5. For an example of the use of this known aldehyde, see: A. B. Smith III, D.-S. Kim, J. Org. Chem. 2006, 71, 2547-2557.
6. For an example of asymmetric aldol reactions, see: D. A. Evans, S. W. Kaldor, T. K. Jones, J. Clardy, T. J. Stout, J. Am. Chem. Soc. 1990, 112, 7001-7031.
7. Formation of the desired anti-anti product was problematic. For example, Roush allylation by using isopropyl (S,S)-tartrate yielded a mixture of the products favoring (1:2) the wrong isomer. For detailed discussions, see: D. A. Evans, B. D. Allison, M. G. Yang, C. E. Masse, J. Am. Chem. Soc. 2001, 123, 10 840-10 852.
8. For the use of magnesium bromide etherate in an allylstannane reaction, see: E. Lee, E. J. Jeong, E. J. Kang, L. T. Sung, S. K. Hong, J. Am. Chem. Soc. 2001, 123, 10 131-10 132.
9. R. D. Walkup, N. U. Obeyesekere, Synthesis 1987, 607-611.
10. For recent examples of β-alkoxyacrylate and β- alkoxymethacrylate radical cyclization, see: a) E. J. Kang, E. J. Cho, M. K. Ji, Y. E. Lee, D. M. Shin, S. Y. Choi, Y. K. Chung, J.-S. Kim, H.-J. Kim, S.-G. Lee, M. S. Lan, E. Lee, J. Org. Chem. 2005, 70, 6321-6329;
11. b) H. Y. Song, J. M. Joo, J. W. Kang, D.-S. Kim, C.-K. Jung, H. S. Kwak, J. H. Park, E. Lee, C. Y. Hong, S. Jeong, K. Jeon, J. H. Park, J. Org. Chem. 2003, 68, 8080-8087;
12. c) E. J. Jeong, E. J. Kang, L. T. Sung, S. K. Hong, E. Lee, J. Am. Chem. Soc. 2002, 124, 14 655-14 662;
13. d) E. Lee, S. J. Choi, H. Kim, H. O. Han, Y. K. Kim, S. J. Min, S. H. Son, S. M. Lim, W. S. Jang, Angew. Chem. 2002, 114, 184-186;
14. Angew. Chem. Int. Ed. 2002, 41, 176-178.
15. E. Lee, S. J. Choi, Org. Lett. 1999, 1, 1127-1128.
16. See, for example: A. Fürstner, J. Mlynarski, M. Albert, J. Am. Chem. Soc. 2002, 124, 10 274-10 275.
17. 17 = + 40.2). The spectral data of the synthetic sample were identical with those of the natural product.
18. For the use of the modified Yamaguchi conditions, see: D. A. Evans, H. P. Ng, D. L. Rieger, J. Am. Chem. Soc. 1993, 115, 11 446-11 459.