A chemoenzymatic total synthesis of the undecenolide (-)-cladospolide C

Australian Journal of Chemistry

Volumn 58, Issue 7, 2005, Pages 511-516

  Banwell, Martin G ^a   Loong, David T J ^a   Willis, Anthony C ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYMES; ESTERS; FUNGI; SINGLE CRYSTALS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

ENANTIOMERS; NATURAL PRODUCTS; RING-CLOSING METATHESIS (RCM); SINGLE-CRYSTAL X-RAY ANALYSIS;

AROMATIC COMPOUNDS;

EID: 23844432200     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH05074     Document Type: Article

References (21)

1. A. Hirota, A. Isogai, H. Sakai, Agric. Biol. Chem. 1981, 45, 799.
2. A. Hirota, H. Sakai, A. Isogai, Agric. Biol. Chem. 1985, 49, 731.
3. Y. Fujii, A. Fukuda, T. Hamasaki, I. Ichimoto, H. Nakajima, Phytochemistry 1995, 40, 1443. doi:10.1016/0031-9422(95)00414-3
4. H. Zhang, H. Tomoda, N. Tabata, H. Miura, M. Namikoshi, Y. Yamaguchi, R. Masuma, S. Omura, J. Antibiot. 2001, 54, 635.
5. (a) A. Hirota, H. Sakai, A. Isogai, Y. Kitano, T. Ashida, H. Hirota, T. Takahashi, Agric. Biol. Chem. 1985, 49, 903.
6. (b) H. Hirota, A. Hirota, H. Sakai, A. Isogai, T. Takahashi, Bull. Chem. Soc. Jpn. 1985, 58, 2147.
7. C. J. Smith, D. Abbanat, V. S. Bernan, W. M. Maiese, M. Greenstein, J. Jompa, A. Tahir, C. M. Ireland, J. Nat. Prod. 2000, 63, 142. doi:10.1021/NP990361W
8. F. Hansske, O. H. Wilhelms, H. Anke, German Pat. DE 3906214 1990.
9. (a) M. G. Banwell, K. A. Jolliffe, D. T. J. Loong, K. J. McRae, F. Vounatsos, J. Chem. Soc., Perkin Trans. 1, 2002, 22.
10. (b) M. G. Banwell, D. T. J. Loong, Org. Biomol. Chem. 2004, 2, 2050. doi:10.1039/B401829J
11. For reviews on methods for generating cis-1,2-dihydrocatechols by microbial dihydroxylation of the corresponding aromatics, as well as the synthetic applications of these metabolities, see: (a) T. Hudlicky, D. Gonzalez, D.T. Gibson, Aldrichim. Acta 1999, 32, 35.
12. (b) M. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, M. D. McLeod, K. J. McRae, S. G. Stewart, M. Vögtle, Pure Appl. Chem. 2003, 75, 223.
13. (c) R. A. Johnson, Org. React. 2004, 63, 117.
14. K. A. B. Austin, M. G. Banwell, D. T. J. Loong, A. D. Rae, A. C. Willis, Org. Biomol. Chem. 2005, 3, 1081. doi:10.1039/B417685E
15. E. L. Dias, S. T. Nguyen, R. H. Grubbs, J. Am. Chem. Soc. 1997, 119, 3887. doi:10.1021/JA963136Z
16. M. G. Banwell, K. J. McRae, Org. Lett. 2000, 2, 3583. doi:10.1021/OL006457V
17. C. C. R. Allen, C. E. Walker, N. D. Sharma, N. A. Kerley, D. R. Boyd, H. Dalton, Biocatal. Biotrans. 2002, 20, 257. doi:10.1080/10242420290029454
18. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923. doi:10.1021/JO00408A041
19. DENZO-SMN: Z. Otwinowski, W. Minor, Processing of X-Ray Diffraction Data Collected in Oscillation Mode, in Methods in Enzymology, Volume 276: Macromolecular Crystallography, Part A (Eds C. W. Carter, Jr, R. M. Sweets) 1997, pp. 307-326 (Academic Press: New York, NY).
20. A. Altomare, M. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435. doi:10.1107/ S002188989400021X
21. P. W. Betteridge, J. R. Carruthers, R. I. Cooper, K. Prout, D. J. Watkin, J. Appl. Crystallogr. 2003, 36, 1487. doi:10.1107/S0021889803021800