A chemoenzymatic total synthesis of the undecenolide (-)-cladospolide B via a mid-stage ring-closing metathesis and a late-stage photo-rearrangement of the E-isomer

Organic and Biomolecular Chemistry

Volumn 3, Issue 6, 2005, Pages 1081-1088

  Austin, Kerrie A B ^a   Banwell, Martin G ^a   Loong, David T J ^a   Rae, A David ^a   Willis, Anthony C ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CHEMICAL BONDS; DIMERS; ESTERS; ISOMERIZATION; ISOMERS; SATURATION (MATERIALS COMPOSITION); SINGLE CRYSTALS; SOLUTIONS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

DOUBLE BONDS; HEAD-TO-HEAD DIMERS; PHOTOISOMERIZATION; RING-CLOSING METATHESIS;

ENZYMES;

CLADOSPOLIDE B; MACROLIDE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLADOSPORIUM; HYDROLYSIS; LIGHT; PHOTOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CLADOSPORIUM; HYDROLYSIS; LIGHT; LIPASE; MACROLIDES; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; STEREOISOMERISM;

EID: 16244381121     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b417685e     Document Type: Article

References (27)

1. A. Hirota, A. Isogai and H. Sakai, Agric. Biol. Chem., 1981, 45, 799.
2. A. Hirota, H. Sakai and A. Isogai, Agric. Biol. Chem., 1985, 49, 731.
3. Y. Fujii, A. Fukuda, T. Hamasaki, I. Ichimoto and H. Nakajima, Phytochemistry, 1995, 40, 1443.
4. H. Zhang, H. Tomoda, N. Tabata, H. Miura, M. Namikoshi, Y. Yamaguchi, R. Masuma and S. Omura, J. Antibiot., 2001, 54, 635.
5. (a) A. Hirota, H. Sakai, A. Isogai, Y. Kitano, T. Ashida, H. Hirota and T. Takahashi, Agric. Biol. Chem., 1985, 49, 903;
6. (b) H. Hirota, A. Hirota, H. Sakai, A. Isogai and T. Takahashi, Bull. Chem. Soc. Jpn., 1985, 58, 2147.
7. (a) C. J. Smith, D. Abbanat, V. S. Bernan, W. M. Maiese, M. Greenstein, J. Jompa, A. Tahir and C. M. Ireland, J. Nat. Prod., 2000, 63, 142;
8. (b) A synthesis of isocladospolide B has been reported but ambiguities still remain regarding the absolute stereochemistries at the three stereogenic centres in this compound: X. Franck, M. E. Vaz Araujo, J.-C. Jullian, R. Hocquemiller and B. Figadere, Tetrahedron Lett., 2001, 42, 2801.
9. F. Hansske, O. H. Wilhelms and H. Anke, Ger. Offen., 1990, DE 3906214.
10. (a) M. G. Banwell, K. A. Jolliffe, D. T. J. Loong, K. J. McRae and F. Vounatsos, J. Chem. Soc., Perkin Trans. 1, 2002, 22;
11. (b) M. G. Banwell and D. T. J. Loong, Org. Biomol Chem., 2004, 2, 2050.
12. (a) M. G. Banwell and D. T. J. Loong, Heterocycles, 2004, 62, 713;
13. (b) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann and R. Mynott, J. Am. Chem. Soc., 2002, 124, 7061;
14. (c) E. Diez, D. J. Dixon, S. V. Ley, A. Polara and F. Rodriguez, Synlett, 2003, 1186 and references cited therein.
15. M. G. Banwell, A. J. Edwards and D. T. J. Loong, ARKIVOC, 2004, x, 53.
16. J.-L. Montchamp, F. Tian, M. E. Hart and J. W. Frost, J. Org. Chem., 1996, 61, 3897.
17. S. V. Ley, H. M. I. Osborn, H. W. M. Priepke and S. L. Warriner, Org. Synth., 1998, 75, 170 and references cited therein.
18. (a) M. Scholl, S. Ding, C. W. Lee and R. H. Grubbs, Org. Lett., 1999, 1, 953;
19. (b) E. L. Dias, S. T. Nguyen and R. H. Grubbs, J. Am. Chem. Soc., 1997, 119, 3887.
20. For an example of such a process carried out within a 17-membered macrolide see: A. K. Ghosh, Y. Wang and J. T. Kim, J. Org. Chem., 2001, 66, 8973.
21. M. G. Banwell and K. J. McRae, Org. Lett., 2000, 2, 3583.
22. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.
23. DENZO-SMN: Z. Otwinowski and W. Minor, 'Processing of X-ray diffraction data collected in oscillation mode', in Macromolecular Crystallography, Part A (Methods Enzymol., vol. 276), eds. C. W. Carter, Jr. and R. M. Sweets, Academic Press, New York, 1997, pp. 307-326.
24. SIR92: A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori and M. Camalli, J. Appl. Crystallogr., 1994, 27, 435.
25. A. D. Rae, RAELS2000, Australian National University, Canberra (Australia), 2000.
26. A. D. Rae, A. C. Willis, D. T. J. Loong and M. G. Banwell, Acta Crystallogr., Sect. B, to be submitted.
27. P. W. Betteridge, J. R. Carruthers, R. I. Cooper, K. Prout and D. J. Watkin, J. Appl. Crystallogr., 2003, 36, 1487.